Herbicidal sulfonamides

ABSTRACT

N-(heterocyclicaminocarbonyl)arylsulfonamides in which at least one of the acyclic nitrogens thereof is substituted by lower alkyl, or sometimes in the case of aminocarbonyl nitrogen, by methoxy; e.g. N-[N-(4,6-dimethoxy-1,3,5-triazin-2-yl)-N-methylaminocarbonyl]-2-chlorobenzenesulfonamide or N-[N-(4,6-dimethoxy-1,3,5-triazin-2-yl)-N-methylaminocarbonyl]-2-nitrobenzenesulfonamide; are useful for the regulation of plant growth and as general and selective herbicides.

This application is a divisional of my copending application U.S. Ser.No. 151,245, filed July 13, 1982 (now U.S. Pat. No. 4,339,266) which inturn is a divisional of application Ser. No. 840,167, filed Oct. 6, 1977(now U.S. Pat. No. 4,257,802).

BACKGROUND

This invention relates to novelN-(heterocyclicaminocarbonyl)arysulfonamides in which at least one ofthe acyclic nitrogens thereof is substituted by lower alkyl, or in somecases by methoxy. The compounds of this invention and theiragriculturally suitable salts, are useful as agricultural chemicals,such as plant growth regulants and herbicides.

Netherlands Pat. No. 121,788, published Sept. 15, 1966, discloses thepreparation of compounds of the following Formula and their use asgeneral or selective herbicides, ##STR1## wherein

R₁ and R₂ may independently be alkyl of 1-4 carbon atoms; and

R₃ and R₄ may independently be hydrogen, chlorine or alkyl of 1-4 carbonatoms.

U.S. Pat. No. 3,637,366 discloses compounds having the formula: ##STR2##wherein

R₁ is hydrogen or lower saturated aliphatic acyl and

R₂ is hydrogen, 2-pyrimidinyl, pyridyl, amidino, acetyl or carbamoyl.The disclosed compounds are said to provide control of crabgrass, cress,endive, clover and Poa annua.

French Pat. No. 1,468,747 discloses the following para-substitutedphenylsulfonamides as being useful as antidiabetic agents: ##STR3##wherein R=H, halogen, CF₃ or alkyl.

Compounds of the following formula, and their use as antidiabeticagents, are reported in J. Drug Res. 6, 123 (1974). ##STR4## wherein Ris pyridyl.

Logemann et al. Chem Ab., 53, 18052 g (1959), disclose a number ofsulfonamides, including uracil derivatives and those having the formula:##STR5## wherein R is butyl, phenyl or ##STR6## and R₁ is hydrogen ormethyl. When tested for hypoglycemic effect in rats (oral doses of 25mg/100 g), the compounds in which R is butyl and phenyl were mostpotent. The others were of low potency or inactive.

Wojciechowski, J. Acta. Polon. Pharm 19, p. 121-5 (1962) [Chem. Ab., 591633 e] describes the synthesis ofN-[(2,6-dimethoxypyrimidin-4-yl)aminocarbonyl]-4-methyl-benzenesulfonamide:##STR7## Based upon similarity to a known compound, the author predictedhypoglycemic activity for the foregoing compound.

Substituted-pyrimidinyl sulfonylureas of the following formula, whichare also para-substituted on the phenyl ring, are disclosed in FarmcoEd. Sci., 12, 586 (1957) [Chem. Ab., 53, 18052 g (1959)]: ##STR8##wherein R=H or CH₃.

The presence of undesired vegetation causes substantial damage to usefulcrops, especially agricultural products that satisfy man's basic foodand fiber needs, such as cotton, rice, corn, wheat, and the like. Thecurrent population explosion and concomitant world food and fibershortage demand improvements in the efficiency of producing these crops.Preventing or minimizing loss of a portion of such valuable crops bykilling, or inhibiting the growth of undesired vegetation is one way ofimproving this efficiency.

A wide variety of materials useful for killing or inhibiting(controlling) the growth of undesired vegetation is available; suchmaterials are commonly referred to as herbicides. However, the needstill exists for effective herbicides that destroy or control weedswhile not significantly damaging useful crops. Some weeds (nutsedge is aparticular example) are very difficult to control; many of theherbicides that are used to control nutsedge are so nonselective thatthey cause damage to the crops themselves.

SUMMARY OF THE INVENTION

According to this invention, there are provided novel compounds ofFormula I and their agriculturally suitable salts, suitable agriculturalcompositions containing them and methods of using them as general andselective herbicides having both preemergence and postemergenceactivity, as well as plant growth regulants. ##STR9## wherein

R₁ is H, alkyl of one to three carbon atoms or --OCH₃ ;

R₂ is H or alkyl of one to three carbon atoms;

R₃ is ##STR10##

R₄ and R₇ are independently hydrogen, fluorine, chlorine, bromine, alkylof 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, nitro, CF₃, CH₃ S-- orCH₃ CH₂ S--;

R₅, R₆ and R₈ are independently hydrogen, fluorine, chlorine, bromine ormethyl;

X is Cl, CH₃, --CH₂ CH₃, alkoxy of one to three carbons, CF₃, CH₃ S--,CH₃ OCH₂ -- or CH₃ OCH₂ CH₂ O--;

Y is CH₃ or OCH₃ ;

Z is CH or N;

and their agriculturally suitable salts; provided that:

(a) R₁ and R₂ may not simultaneously be hydrogen; and

(b) when R₄ and R₈ are both hydrogen, at least one of R₅, R₆ or R₇ mustbe hydrogen;

(c) when R₆ os other than H, at least one or R₄, R₅, R₇ and R₈ is otherthan H and at least two of R₄, R₅, R₇ and R₈ must be hydrogen; and

(d) when R₆ is H and all of R₄, R₅, R₇ and R₈ are other than H, then allof R₄, R₅, R₇ and R₈ must be either Cl or CH₃.

Preferred in order of increasing preference based on activity or cost,or both, are:

(1) those compounds of Formula I defined above wherein

R₁ and R₂ are independently H or CH₃ ;

X is CH₃, CH₃ CH₂ -- or alkoxy of one to three carbons; and

Y is CH₃ or OCH₃ ;

(2) compounds of preference (1) wherein

X and Y are independently CH₃ or OCH₃ ;

R₁ is CH₃ ; and

R₂ is H;

(3) compounds of preference (2) wherein

X is OCH₃ ; and

Y is CH₃ or OCH₃ ;

(4) compounds of Formula I wherein

R₃ is ##STR11##

(5) compounds of preferance (4) wherein

R₃ is ##STR12##

(6) compounds of preference (5) wherein

R₄ is Cl, CH₃ or NO₂ ; and

R₇ is H, Cl or CH₃ ;

(7) compounds of Formula I defined above wherein

R₁ is CH₃ ;

R₂ is H; ##STR13## R₄ is Cl, CH₃ or NO₂ ; R₇ is H, Cl or CH₃ ;

X is OCH₃ ; and

Y is CH₃ or OCH₃.

Specifically preferred for their outstanding herbicidal activity, orvery favorable cost, or both, are:

(1)N-[N-(4,6-dimethoxy-1,3,5-triazin-2-yl)-N-methylaminocarbonyl]-2-chlorobenzenesulfonamide.

(2)N-[N-(4,6-dimethoxy-1,3,5-triazin-2-yl)-N-methylaminocarbonyl]-2-nitrobenzenesulfonamide.

(3)N-[N-(4-(4-methoxy-6-methylpyrimidin-2-yl)-N-methylaminocarbonyl]-2-chlorobenzenesulfonamide.

(4)N-[N-(4-methoxy-6-methylpyrimidin-2-yl)-N-methylaminocarbonyl]-2-nitrobenzenesulfonamide.

Synthesis

As shown in Equation 1, the compounds of Formula I, wherein R₂ is H, canbe prepared by reacting an appropriately substituted sulfonyl isocyanateof Formula II with an appropriate 2-alkylaminopyrimidine or2-alkylamino-1,3,5-triazine of Formula III, R₁, R₃, X, Y and Z being aspreviously defined.

Equation 1 ##STR14##

The reaction is best carried out in inert aprotic organic solvents suchas methylene chloride, tetrahydrofuran or acetonitrile, at ambientpressure and temperature. The mode of addition is not critical; however,it is often convenient to add the sulfonyl isocyanate to a stirredsuspension of amine III. Since each isocyanates usually are liquids,their addition can be easily controlled.

The reaction is generally exothermic. In some cases, the desired productis insoluble in the warm reaction medium and crystallizes from it inpure form. Products soluble in the reaction medium are isolated byevaporation of the solvent, trituration of the solid residue withsolvents such as 1-chlorobutane or ethyl ether, and filtration.

Compounds of Formula I, wherein R₂ is alkyl, can be prepared byalkylation of the salts of compounds of Formula I, wherein R₂ is H, asshown in Equation 2; R₁, R₂, R₃, X, Y and Z being as previously definedand M is a metal cation and Q an anion, such as halide or sulfate.

Equation 2 ##STR15##

The reaction is best carried out in aprotic organic solvents such astetrahydrofuran, dimethylformamide, or dimethylacetamide, at ambientpressure and temperature. Alkylating agents such as dimethyl sulfate,methyl iodide, and ethyl iodide can be employed. The desired product canbe isolated by pouring the reaction mixture into water and filtering offthe precipitated solid.

Alternatively, compounds of Formula I, wherein R₂ is alkyl, can beprepared by the reaction of an appropriately substitutedsulfonyl-N-alkylcarbamyl chloride of Formula IV with an appropriate2-aminopyrimidine or 2-amino-1,3,5-triazine of Formula III; as shown inEquation 3; R₁, R₂, R₃, A, X and Z are as previously defined.

Equation 3 ##STR16##

The preparation of ureas from amines and carbamyl chlorides is wellknown to the art. The reaction can best be carried out by addingequivalent amounts of a carbamyl chloride, IV, and amine, III, to aninert organic solvent, such as tetrahydrofuran, xylene, or methylenechloride, in the presence of acid acceptor, such as triethylamine,pyridine, or sodium carbonate employing temperatures from 20°-130°.Soluble products can be isolated by filtering off precipitated salts andconcentration of the filtrate. Insoluble products can be filtered offand washed free of salts with water.

The intermediate sulfonyl-N-alkyl carbamyl chlorides of Formula IV canbe prepared by phosgenation of N-alkylsulfonamide salts. The sulfonamidesalt is added to an excess of phosgene in an inert organic solvent, suchas tetrahydrofuran, toluene, or xylene, whereupon the carbamyl chloridecan be isolated or reacted in situ with the amine, III, after removal ofthe excess phosgene.

The preparation of agriculturally suitable salts of the compounds ofFormula I, as well as starting materials and intermediates for saidcompounds is disclosed in my applications Ser. No. 824,805 filed Aug.15, 1977 and Ser. No. 840,389 filed Oct. 6, 1977, the contents of whichare incorporated by reference.

The compounds of this invention and their preparation are furtherillustrated by the following examples wherein temperatures are given indegrees centigrade.

EXAMPLE 1N-[N-(4,6-dimethoxy-1,3,5-triazin-2-yl)-N-methylaminocarbonyl]-2-chlorobenzenesulfonamide

To a dry, well-stirred mixture of 1.7 g of2-methylamino-4,6-dimethoxy-1,3,5-triazine in 25 ml of acetonitrile, atambient pressure and temperature, was added dropwise 2.2 g of2-chlorobenzenesulfonyl isocyanate. The resulting mixture was stirredfor 18 hours and the precipitated product removed by filtration to yield2.5 g of white crystals melting at 52°-56°. The product wasN-[N-(4,6-dimethoxy-1,3,5-triazin-2-yl)-N-methylaminocarbonyl]-2-chlorobenzenesulfonamide.

EXAMPLE 2N-[N-(4,6-dimethoxy-1,3,5-triazin-2-yl)-N-methylaminocabonyl]-2-nitrobenzenesulfonamide

To a mixture of 1.7 g of 2-methylamino-4,6-dimethoxy-1,3,5-triazine in50 ml of acetonitrile was added 2.3 g of 2-nitrobenzenesulfonylisocyanate with stirring. The resultant mixture was stirred at ambienttemperature for 72 hours and filtered to afford 1.2 g of a whitecrystalline solid melting at 184°-186°. The product wasN-[N-(4,6-dimethoxy-1,3,5-triazin-2-yl)-N-methylaminocarbonyl]-2-nitrobenzenesulfonamidewhich showed characteristic infrared absorption peaks at 1710 cm⁻¹, 1590cm⁻¹, and 1550 cm⁻¹.

By using equivalent amounts of an appropriate2-alkylamino-1,3,5-triazine and an appropriately substitutedbenzenesulfonyl isocyanate, the compounds of Formula I set forth inTable I can be prepared by the procedures of Examples 1 or 2.

                  TABLE (I-A)                                                     ______________________________________                                         ##STR17##                                                                    R.sub.1   R.sub.4    R.sub.5 R.sub.6                                                                            R.sub.7                                                                              R.sub.8                              ______________________________________                                        CH.sub.3  Br         H       H    H      H                                    CH.sub.3  OCH.sub.3  H       H    OCH.sub.3                                                                            H                                    CH.sub.3  Cl         H       H    Cl     H                                    CH.sub.3  CH.sub.3   H       H    H      H                                    CH.sub.3  CH.sub.3   H       H    CH.sub.3                                                                             H                                    CH.sub.3  H          H       H    H      H                                    CH.sub.3  Cl         H       H    H      Cl                                   CH.sub.3  F          H       H    H      H                                    CH.sub.3  CF.sub.3   H       H    H      H                                    C.sub.2 H.sub.5                                                                         Cl         H       H    H      H                                    C.sub.2 H.sub.5                                                                         NO.sub.2   H       H    Cl     H                                    C.sub.2 H.sub.5                                                                         Cl         H       H    Cl     H                                    C.sub.2 H.sub.5                                                                         CH.sub.3   H       H    H      H                                    n-C.sub.3 H.sub.7                                                                       Cl         H       H    OCH.sub.3                                                                            H                                    n-C.sub.3 H.sub.7                                                                       NO.sub.2   H       H    H      H                                    CH(CH.sub.3).sub.2                                                                      Cl         H       H    H      H                                    CH(CH.sub.3).sub.2                                                                      NO.sub.2   H       H    H      H                                    OCH.sub.3 CF.sub.3   H       H    H      H                                    OCH.sub.3 Cl         H       H    H      H                                    OCH.sub.3 CH.sub.3   H       H    H      H                                    OCH.sub.3 Cl         H       H    H      Cl                                   CH.sub.3  OC.sub.2 H.sub.5                                                                         H       H    OC.sub.2 H.sub.5                                                                     H                                    CH.sub.3  C.sub.2 H.sub.5                                                                          H       H    C.sub.2 H.sub.5                                                                      H                                    CH.sub.3  CH(CH.sub.3).sub.2                                                                       H       H    H      H                                    CH.sub.3  Br         H       H    Br     H                                    C.sub.2 H.sub.5                                                                         F          H       H    F      H                                    C.sub.2 H.sub.5                                                                         CF.sub.3   H       H    H      H                                    CH.sub.3  CH.sub.3   CH.sub.3                                                                              H    CH.sub.3                                                                             CH.sub.3                             CH.sub.3  H          F       H    H      H                                    CH.sub.3  Cl         H       F    H      H                                    CH.sub.3  H          Cl      H    H      H                                    CH.sub.3  SCH.sub.3  H       H    H      H                                    ______________________________________                                    

                  TABLE (I-B)                                                     ______________________________________                                         ##STR18##                                                                    R.sub.1   R.sub.4    R.sub.5 R.sub.6                                                                            R.sub.7 R.sub.8                             ______________________________________                                        CH.sub.3  Cl         H       H    H       H                                   CH.sub.3  NO.sub.2   H       H    H       H                                   CH.sub.3  CH.sub.3   H       H    H       H                                   CH.sub.3  Cl         H       H    Cl      H                                   CH.sub.3  Cl         H       H    H       Cl                                  CH.sub.3  CH.sub.3   H       H    CH.sub.3                                                                              H                                   CH.sub.3  H          H       H    H       H                                   CH.sub.3  OCH.sub.3  H       H    OCH.sub.3                                                                             H                                   CH.sub.3  F          H       H    H       F                                   C.sub.2 H.sub.5                                                                         NO.sub.2   H       H    H       H                                   CH(CH.sub.3).sub.2                                                                      Cl         H       H    H       H                                   CH(CH.sub.3).sub.2                                                                      Cl         H       H    Cl      H                                   C.sub.2 H.sub.5                                                                         CH.sub.3   H       H    H       H                                   C.sub.2 H.sub.5                                                                         F          H       H    H       H                                   C.sub.2 H.sub.5                                                                         F          H       H    H       F                                   C.sub.2 H.sub.5                                                                         Br         H       H    H       H                                   C.sub.2 H.sub.5                                                                         OC.sub.2 H.sub.5                                                                         H       H    OC.sub.2 H.sub.5                                                                      H                                   OCH.sub.3 Cl         H       H    H       H                                   OCH.sub.3 NO.sub.2   H       H    H       H                                   OCH.sub.3 Cl         H       H    Cl      H                                   OCH.sub.3 F          H       H    H       F                                   CH.sub.3  CH.sub.3   H       H    CH.sub.3                                                                              H                                   n-C.sub.3 H.sub.7                                                                       CH.sub.3   H       H    H       H                                   n-C.sub.3 H.sub.7                                                                       OCH.sub.3  H       H    OCH.sub.3                                                                             H                                   n-C.sub.3 H.sub.7                                                                       F          H       H    H       H                                   CH.sub.3  SCH.sub.3  H       H    H       H                                   CH.sub.3  Cl         H       F    H       H                                   CH.sub.3  Cl         H       H    OCH.sub.3                                                                             H                                   CH.sub.3  n-C.sub.3 H.sub.7 O                                                                      H       H    n-C.sub.3 H.sub.7 O                                                                   H                                   CH.sub.3  H          F       H    H       H                                   CH.sub.3  Cl         H       H    NO.sub.2                                                                              H                                   CH.sub.3  CH.sub.3   CH.sub.3                                                                              H    CH.sub.3                                                                              CH.sub.3                            CH.sub.3  SCH.sub.2 CH.sub.3                                                                       H       H    H       H                                   ______________________________________                                    

                  TABLE (I-C)                                                     ______________________________________                                         ##STR19##                                                                    R.sub.1   R.sub.4   R.sub.5 R.sub.6                                                                            R.sub.7 R.sub.8                              ______________________________________                                        CH.sub.3  Cl        H       H    H       H                                    CH.sub.3  NO.sub.2  H       H    H       H                                    CH.sub.3  CH.sub.3  H       H    H       H                                    CH.sub.3  Cl        H       H    Cl      H                                    CH.sub.3  CH.sub.3  H       H    CH.sub.3                                                                              H                                    CH.sub.3  H         H       H    H       H                                    C.sub.2 H.sub.5                                                                         NO.sub.2  H       H    H       H                                    CH(CH.sub.3).sub.2                                                                      Cl        H       H    Cl      H                                    n-C.sub.3 H.sub.7                                                                       Cl        H       H    H       H                                    CH.sub.3  OCH.sub.3 H       H    H       H                                    CH.sub.3  OCH.sub.3 H       H    OCH.sub.3                                                                             H                                    C.sub.2 H.sub.5                                                                         SCH.sub.3 H       H    H       H                                    C.sub.2 H.sub.5                                                                         F         H       H    H       H                                    C.sub.2 H.sub.5                                                                         Cl        H       H    Cl      H                                    C.sub.2 H.sub.5                                                                         Br        H       H    H       H                                    C.sub.2 H.sub.5                                                                         CF.sub.3  H       H    H       H                                    n-C.sub.3 H.sub.7                                                                       CH.sub.3  H       H    H       H                                    n-C.sub.3 H.sub.7                                                                       NO.sub.2  H       H    H       H                                    CH.sub.3  CH.sub.3  CH.sub.3                                                                              H    CH.sub.3                                                                              CH.sub.3                             CH.sub.3  C.sub.2 H.sub.5                                                                         H       H    H       H                                    CH.sub.3  OC.sub.2 H.sub.5                                                                        H       H    OC.sub.2 H.sub.5                                                                      H                                    CH.sub.3  n-C.sub.4 H.sub.9 O                                                                     H       H    n-C.sub.4 H.sub.9 O                                                                   H                                    CH.sub.3  Cl        H       H    OCH.sub.3                                                                             H                                    CH.sub.3  H         F       H    H       H                                    CH.sub.3  SC.sub.2 H.sub.5                                                                        H       H    H       H                                    OCH.sub.3 Cl        H       H    H       H                                    OCH.sub.3 F         H       H    H       H                                    OCH.sub.3 F         H       H    H       F                                    OCH.sub.3 CH.sub.3  H       H    H       H                                    OCH.sub.3 Cl        H       H    Cl      H                                    CH.sub.3  F         H       F    H       F                                    CH.sub.3  Br        H       H    H       H                                    CH.sub.3  Cl        Cl      H    H       H                                    CH.sub.3  i-C.sub.3 H.sub.7 O                                                                     H       H    i-C.sub.3 H.sub.7 O                                                                   H                                    ______________________________________                                    

                  TABLE (I-D)                                                     ______________________________________                                         ##STR20##                                                                    R.sub.1                                                                             R.sub.4  R.sub.5                                                                              R.sub.6                                                                            R.sub.7                                                                              R.sub.8                                                                           X                                       ______________________________________                                        CH.sub.3                                                                            Cl       H      H    H      H   C.sub.2 H.sub.5                         CH.sub.3                                                                            NO.sub.2 H      H    H      H   C.sub.2 H.sub.5                         CH.sub.3                                                                            Cl       H      H    N      H   OC.sub.2 H.sub.5                        CH.sub.3                                                                            CH.sub.3 H      H    CH.sub.3                                                                             H   CF.sub.3                                CH.sub.3                                                                            F        H      H    H      H   SCH.sub.3                               CH.sub.3                                                                            Cl       H      H    H      Cl  CH.sub.2 OCH.sub.3                      C.sub.2 H.sub.5                                                                     NO.sub.2 H      H    H      H   OC.sub.2 H.sub.5                        C.sub.2 H.sub.5                                                                     Cl       H      H    H      H   C.sub.2 H.sub.5                         CH.sub.3                                                                            NO.sub.2 H      H    H      H   Cl                                      CH.sub.3                                                                            Cl       H      H    Cl     H   Cl                                      CH.sub.3                                                                            CH.sub.3 H      H    H      H   OCH.sub.2 CH.sub.2 OCH.sub.3            CH.sub.3                                                                            OCH.sub.3                                                                              H      H    OCH.sub.3                                                                            H   n-C.sub.3 H.sub.7 O                     CH.sub.3                                                                            Br       H      H    H      H   CF.sub.3                                CH.sub.3                                                                            H        F      H    H      H   OC.sub.2 H.sub.5                        C.sub.2 H.sub.5                                                                     NO.sub.2 H      H    H      H   SCH.sub.3                               C.sub.2 H.sub.5                                                                     OC.sub.2 H.sub.5                                                                       H      H    OC.sub.2 H.sub.5                                                                     H   OC.sub.2 H.sub.5                        C.sub.2 H.sub.5                                                                     Br       H      H    H      H   OC.sub.2 H.sub.5                        C.sub.2 H.sub.5                                                                     Cl       H      H    Cl     H   C.sub.2 H.sub.5                         n-C.sub.3 H.sub.7                                                                   Cl       H      H    H      H   CH.sub.2 OCH.sub.3                      n C.sub.3 H.sub.7                                                                   CH.sub.3 H      H    H      H   SCH.sub.3                               i C.sub.3 H.sub.7                                                                   F        H      H    H      F   OCH.sub.2 CH.sub.2 OCH.sub.3            i-C.sub.3 H.sub.7                                                                   CF.sub.3 H      H    H      H   OC.sub.2 H.sub.5                        OCH.sub.3                                                                           F        H      H    H      H   C.sub.2 H.sub.5                         ______________________________________                                    

                  TABLE (I-E)                                                     ______________________________________                                         ##STR21##                                                                    R.sub.1  R.sub.4  R.sub.5                                                                             R.sub.6                                                                           R.sub.7                                                                             R.sub.8                                                                           X                                       ______________________________________                                        CH.sub.3 Cl       H     H   H     H   C.sub.2 H.sub.5                         CH.sub.3 NO.sub.2 H     H   H     H   C.sub.2 H.sub.5                         CH.sub.3 Cl       H     H   H     Cl  OC.sub.2 H.sub.5                        CH.sub.3 OCH.sub.3                                                                              H     H   OCH.sub.3                                                                           H   OC.sub.2 H.sub.5                        CH.sub.3 Cl       H     H   H     H   Cl                                      CH.sub.3 NO.sub.2 H     H   H     H   Cl                                      CH.sub.3 Cl       H     H   H     Cl  CH.sub.2 OCH.sub.3                      CH.sub.3 F        H     H   H     H   SCH.sub.3                               C.sub.2 H.sub.5                                                                        NO.sub.2 H     H   H     H   OC.sub.2 H.sub. 5                       C.sub.2 H.sub.5                                                                        Cl       H     H   H     H   OC.sub.2 H.sub.5                        CH(CH.sub.3).sub.2                                                                     CH.sub.3 H     H   H     H   OC.sub.2 H.sub.5                        CH(CH.sub.3).sub.2                                                                     F        H     H   H     F   OCH.sub.2 CH.sub.2 OCH.sub.3            C.sub.2 H.sub.5                                                                        Br       H     H   H     H   C.sub.2 H.sub.5                         C.sub.2 H.sub.5                                                                        OCH.sub.3                                                                              H     H   H     H   n-C.sub.3 H.sub.7 O                     C.sub.2 H.sub.5                                                                        CH.sub.3 H     H   CH.sub.3                                                                            H   C.sub.2 H.sub.5                         n-C.sub.3 H.sub.7                                                                      Cl       H     H   Cl    H   CF.sub.3                                n-C.sub.3 H.sub.7                                                                      OCH.sub.3                                                                              H     H   OCH.sub.3                                                                           H   Cl                                      n-C.sub.3 H.sub.7                                                                      F        H     H   F     H   OC.sub.2 H.sub.5                        CH.sub.3 H        H     H   H     H   CH.sub.2 OCH.sub.3                      CH.sub.3 CH.sub.3 H     H   NO.sub.2                                                                            H   SCH.sub.3                               CH.sub.3 CF.sub.3 H     H   H     H   OCH.sub.2 CH.sub.2 OCH.sub.3            CH.sub.3 OC.sub.2 H.sub.5                                                                       H     H   OC.sub.2 H.sub.5                                                                    H   C.sub.2 H.sub.5                         CH.sub.3 SCH.sub.2 CH.sub.3  H                                                                    H     H     H   OC.sub.2 H.sub.5                          OCH.sub. 3                                                                             F        H     H   H     H   C.sub.2 H.sub.5                         ______________________________________                                    

EXAMPLE 3N-[N-(4-methoxy-6-methylpyrimidin-2-yl)-N-methylaminocarbonyl]-2,5-dichlorobenzenesulfonamide

To a stirred mixture of 0.8 g of2-methylamino-4-methoxy-6-methylpyrimidine in 25 ml of acetonitrilecontaining a few crystals of 1,4-diazabicyclo[2.2.2]octane was addeddropwise 1.3 g of 2,5-dichlorobenzenesulfonyl isocyanate. The mixturewas stirred for 16 hours and the resultant solid was filtered to afford1.2 g ofN-[N-(4-methoxy-6-methylpyrimidine-2-yl)-N-methylaminocarbonyl]-2,5-dichlorobenzenesulfonamidemelting at 182°-185°. Infrared absorption spectrum showed peaks at 1690cm⁻¹, 1590 cm⁻¹, and 1550 cm⁻¹ which are typical for this type ofcompound.

EXAMPLE 4N-[N-(4-methoxy-6-methylpyrimidin-2-yl)-N-methylaminocarbonyl]-2,6-dichlorobenzenesulfonamide

To 0.8 g of 4-methoxy-6-methyl-2-methylaminopyrimidine in 25 ml of dryacetonitrile containing a few crystals of 1,4-diazabicyclo[2.2.2]octanewas added 1.3 g of 2,6-dichlorobenzenesulfonyl isocyanate. The mixturewas stirred at ambient temperature for 16 hours and the resultantsolution was evaporated leaving a white solid. Trituration with1-chlorobutane followed by filtration afforded 0.5 g ofN-[N-(4-methoxy-6-methylpyrimidine-2-yl)-N-methylaminocarbonyl]-2,6-dichlorobenzenesulfonamidemelting at 170°-171°. Infrared absorption peaks were observed at 1700cm⁻¹, 1600 cm⁻¹, and 1570 cm⁻¹.

By using equivalent amounts of an appropriate 2-alkylaminopyrimidine andan appropriately substituted benzenesulfonyl isocyanate, the compoundsof Formula I set forth in Table II can be prepared by the procedures ofExamples 3 and 4.

                  TABLE (II-A)                                                    ______________________________________                                         ##STR22##                                                                    R.sub.1  R.sub.4    R.sub.5                                                                              R.sub.6                                                                           R.sub.7                                                                              R.sub.8                                                                            m.p.                               ______________________________________                                        CH.sub.3 Cl         H      H   H      H    168-                                                                          170°                        CH.sub.3 CH.sub.3   H      H   H      H                                       CH.sub.3 NO.sub.2   H      H   H      H                                       CH.sub.3 F          H      H   H      H                                       CH.sub.3 CH.sub.3   H      H   CH.sub.3                                                                             H                                       CH.sub.3 OCH.sub.3  H      H   OCH.sub.3                                                                            H                                       CH.sub.3 CF.sub.3   H      H   H      H                                       CH.sub.3 H          H      H   H      H                                       CH.sub.3 OCH.sub.3  H      H   Cl     H                                       C.sub.2 H.sub.5                                                                        Cl         H      H   H      H                                       C.sub.2 H.sub.5                                                                        Cl         H      H   Cl     H                                       CH(CH.sub.3 ).sub.2                                                                    NO.sub.2   H      H   H      H                                       n-C.sub.3 H.sub.7                                                                      Cl         H      H   H      Cl                                      OCH.sub.3                                                                              NO.sub.2   H      H   H      H                                       OCH.sub.3                                                                              CH.sub.3   H      H   H      H                                       OCH.sub.3                                                                              CF.sub.3   H      H   H      H                                       OCH.sub.3                                                                              Cl         H      H   NO.sub.2                                                                             H                                       OCH.sub.3                                                                              F          H      H   F      H                                       n-C.sub.3 H.sub.7                                                                      F          H      H   H      F                                       CH(CH.sub.3).sub.2                                                                     CF.sub.3   H      H   H      H                                       CH(CH.sub.3).sub.2                                                                     Cl         H      H   OCH.sub.3                                                                            H                                       n-C.sub.3 H.sub.7                                                                      CH.sub.3   H      H   H      H                                       C.sub.2 H.sub.5                                                                        OCH.sub.3  H      H   Cl     H                                       C.sub.2 H.sub.5                                                                        H          F      H   H      H                                       C.sub.2 H.sub.5                                                                        CH.sub.3   CH.sub.3                                                                             H   CH.sub.3                                                                             CH.sub.3                                C.sub.2 H.sub.5                                                                        CH(CH.sub.3).sub.2                                                                       H      H   H      H                                       C.sub.2 H.sub.5                                                                        OC.sub.2 H.sub.5                                                                         H      H   OC.sub.2 H.sub.5                                                                     H                                       CH.sub.3 SCH.sub.3  H      H   H      H                                       CH.sub.3 SC.sub.2 H.sub.5                                                                         H      H   H      H                                       CH.sub.3 C.sub.3 H.sub.7 O                                                                        H      H   n-C.sub.3 H.sub.7 O                                                                  H                                       CH.sub.3 H          Cl     H   H      H                                       CH.sub.3 C.sub.2 H.sub.5                                                                          H      H   C.sub.2 H.sub.5                                                                      H                                       CH.sub.3 Br         H      H   Br     H                                       CH.sub.3 Cl         H      F   H      H                                       CH.sub.3 Cl         Cl     H   Cl     Cl                                      CH.sub.3 CH.sub.3   H      H   Cl     H                                       ______________________________________                                    

                  TABLE (II-B)                                                    ______________________________________                                         ##STR23##                                                                    R.sub.1  R.sub.4  R.sub.5                                                                              R.sub.6                                                                            R.sub.7                                                                              R.sub.8                                                                            m.p.                                ______________________________________                                        CH.sub.3 H        H      H    H      H    146-147                             CH.sub.3 Cl       H      H    H      H                                        CH.sub.3 NO.sub.2 H      H    H      H                                        CH.sub.3 Cl       H      H    Cl     H                                        CH.sub.3 Cl       H      H    H      Cl                                       CH.sub.3 CH.sub.3 H      H    H      H                                        CH.sub.3 CH.sub.3 H      H    CH.sub.3                                                                             H                                        CH.sub.3 OCH.sub.3                                                                              H      H    OCH.sub.3                                                                            H                                        CH.sub.3 F        H      H    H      H                                        CH.sub.3 OCH.sub.3                                                                              H      H    Cl     H                                        CH.sub.3 CF.sub.3 H      H    H      H                                        C.sub.2 H.sub.5                                                                        Cl       H      H    H      H                                        C.sub.2 H.sub.5                                                                        Cl       H      H    Cl     H                                        C.sub.2 H.sub.5                                                                        H        F      H    H      H                                        C.sub.2 H.sub.5                                                                        CH.sub.3 CH.sub.3                                                                             H    CH.sub.3                                                                             CH.sub.3                                 C.sub.2 H.sub.5                                                                        OC.sub.2 H.sub.5                                                                       H      H    OC.sub.2 H.sub.5                                                                     H                                        C.sub.2 H.sub.5                                                                        OCH.sub.3                                                                              H      H    Cl     H                                        C.sub.2 H.sub.5                                                                        Br       H      H    H      H                                        n-C.sub.3 H.sub.7                                                                      CH.sub.3 H      H    H      H                                        n-C.sub.3 H.sub.7                                                                      F        H      H    H      F                                        n-C.sub.3 H.sub.7                                                                      Cl       H      H    H      Cl                                       CH(CH.sub.3).sub.2                                                                     CF.sub.3 H      H    H      H                                        CH(CH.sub.3).sub.2                                                                     Cl       H      H    OCH.sub.3                                                                            H                                        CH(CH.sub.3).sub.2                                                                     NO.sub.2 H      H    H      H                                        OCH.sub.3                                                                              NO.sub.2 H      H    H      H                                        OCH.sub.3                                                                              CH.sub.3 H      H    H      H                                        OCH.sub.3                                                                              CF.sub.3 H      H    H      H                                        OCH.sub.3                                                                              Cl       H      H    NO.sub.2                                                                             H                                        OCH.sub.3                                                                              F        H      H    F      H                                        CH.sub.3 SCH.sub.3                                                                              H      H    H      H                                        CH.sub.3 SC.sub.2 H.sub.5                                                                       H      H    H      H                                        CH.sub.3 n-C.sub.3 H.sub.7 O                                                                    H      H    n-C.sub.3 H.sub.7 O                                                                  H                                        CH.sub.3 H        Cl     H    H      H                                        CH.sub. 3                                                                              C.sub.2 H.sub.5                                                                        H      H    C.sub.2 H.sub.5                                                                      H                                        CH.sub.3 Br       H      H    Br     H                                        CH.sub.3 Cl       H      F    H      H                                        CH.sub.3 Cl       Cl     H    Cl     Cl                                       CH.sub.3 CH.sub.3 H      H    Cl     H                                        ______________________________________                                    

                  TABLE (II-C)                                                    ______________________________________                                         ##STR24##                                                                    R.sub.1   R.sub.4   R.sub.5 R.sub.6                                                                            R.sub.7 R.sub.8                              ______________________________________                                        CH.sub.3  Cl        H       H    H       H                                    CH.sub.3  Cl        H       H    Cl      H                                    CH.sub.3  Cl        H       H    H       Cl                                   CH.sub.3  NO.sub.2  H       H    H       H                                    CH.sub.3  CH.sub.3  H       H    H       H                                    CH.sub.3  CH.sub.3  H       H    CH.sub.3                                                                              H                                    CH.sub.3  OCH.sub.3 H       H    OCH.sub.3                                                                             H                                    CH.sub.3  F         H       H    H       H                                    CH.sub.3  OCH.sub.3 H       H    Cl      H                                    C.sub.2 H.sub.5                                                                         Cl        H       H    H       H                                    C.sub.2 H.sub.5                                                                         H         F       H    H       H                                    CH(CH.sub.3).sub.2                                                                      CF.sub.3  H       H    H       H                                    CH(CH.sub.3).sub.2                                                                      Cl        H       H    OCH.sub.3                                                                             H                                    n-C.sub.3 H.sub.7                                                                       F         H       H    H       F                                    n-C.sub.3 H.sub.7                                                                       Cl        H       H    H       Cl                                   n-C.sub.3 H.sub.7                                                                       CH.sub.3  H       H    H       H                                    C.sub.2 H.sub.5                                                                         H         Cl      H    H       H                                    C.sub.2 H.sub.5                                                                         CH.sub.3  CH.sub.3                                                                              H    CH.sub.3                                                                              CH.sub.3                             C.sub.2 H.sub.5                                                                         OC.sub.2 H.sub.5                                                                        H       H    OC.sub.2 H.sub.5                                                                      H                                    C.sub.2 H.sub.5                                                                         OCH.sub.3 H       H    Cl      H                                    C.sub.2 H.sub.5                                                                         Br        H       H    H       H                                    CH(CH.sub.3).sub.2                                                                      NO.sub.2  H       H    Cl      H                                    OCH.sub.3 NO.sub.2  H       H    H       H                                    OCH.sub.3 CH.sub.3  H       H    H       H                                    OCH.sub.3 CF.sub.3  H       H    H       H                                    OCH.sub.3 Cl        H       H    NO.sub.2                                                                              H                                    OCH.sub.3 F         H       H    F       H                                    CH.sub.3  SCH.sub.3 H       H    H       H                                    CH.sub.3  SC.sub.2 H.sub.5                                                                        H       H    H       H                                    CH.sub.3  n-C.sub.3 H.sub.7 O                                                                     H       H    n-C.sub.3 H.sub.7 O                                                                   H                                    CH.sub.3  H         Cl      H    H       H                                    CH.sub.3  H         H       F    H       H                                    CH.sub.3  C.sub.2 H.sub.5                                                                         H       H    C.sub.2 H.sub.5                                                                       H                                    CH.sub. 3 Br        H       H    Br      H                                    CH.sub.3  Cl        H       F    H       H                                    CH.sub.3  Cl        Cl      H    Cl      Cl                                   CH.sub.3  CH.sub.3  H       H    Cl      H                                    ______________________________________                                    

                  TABLE (II-D)                                                    ______________________________________                                         ##STR25##                                                                      R.sub.1     R.sub.4 R.sub.5                                                                           R.sub.6                                                                           R.sub.7                                                                             R.sub.8                                                                           X                                     ______________________________________                                        CH.sub.3  Cl      H     H   H     H   C.sub.2 H.sub.5                         CH.sub.3  NO.sub.2                                                                              H     H   H     H   C.sub.2 H.sub.5                         CH.sub.3  Cl      H     H   Cl    H   OC.sub.2 H.sub.5                        CH.sub.3  CH.sub.3                                                                              H     H   CH.sub.3                                                                            H   CF.sub.3                                CH.sub.3  F       H     H   H     H   SCH.sub.3                               CH.sub.3  Cl      H     H   H     Cl  CH.sub.2 OCH.sub.3                      CH.sub.3  NO.sub.2                                                                              H     H   H     H   Cl                                      CH.sub.3  Cl      H     H   Cl    H   Cl                                      CH.sub.3  CH.sub.3                                                                              H     H   H     H   OCH.sub.2 CH.sub.2 OCH.sub.3            CH.sub.3  Br      H     H   H     H   n-C.sub.3 H.sub.7 O                     CH.sub.3  H       F     H   H     H   CF.sub.3                                CH.sub.3  OCH.sub.3                                                                             H     H   OCH.sub.3                                                                           H   OC.sub.2 H.sub.5                        C.sub.2 H.sub.5                                                                         NO.sub.2                                                                              H     H   H     H   OC.sub.2 H.sub.5                        C.sub.2 H.sub.5                                                                         Cl      H     H   H     H   C.sub.2 H.sub.5                         C.sub.2 H.sub.5                                                                         CH.sub.3                                                                              H     H   H     H   SCH.sub.3                               C.sub.2 H.sub.5                                                                         OC.sub.2 H.sub.5                                                                      H     H   OC.sub.2 H.sub.5                                                                    H   OC.sub.2 H.sub.5                        C.sub.2 H.sub.5                                                                         Cl      H     H   Cl    H   CF.sub.3                                n-C.sub.3 H.sub.7                                                                       Cl      H     H   H     H   CH.sub.2 OCH.sub.3                      n-C.sub.3 H.sub.7                                                                       CH.sub.3                                                                              H     H   Cl    H   SCH.sub.3                               CH(CH.sub.3).sub.2                                                                      F       H     H   H     F   OCH.sub.2 CH.sub.2 OCH.sub.3            CH(CH.sub.3).sub.2                                                                      CF.sub.3                                                                              H     H   H     H   OC.sub.2 H.sub.5                        OCH.sub.3 F       H     H   H     H   C.sub.2 H.sub.5                         ______________________________________                                    

                  TABLE (II-E)                                                    ______________________________________                                         ##STR26##                                                                      R.sub.1     R.sub.4 R.sub.5                                                                           R.sub.6                                                                           R.sub.7                                                                             R.sub.8                                                                           X                                     ______________________________________                                        CH.sub.3  Cl      H     H   H     H   C.sub.2 H.sub.5                         CH.sub.3  NO.sub.2                                                                              H     H   H     H   C.sub.2 H.sub.5                         CH.sub.3  Cl      H     H   H     Cl  OC.sub.2 H.sub.5                        CH.sub.3  OCH.sub.3                                                                             H     H   OCH.sub.3                                                                           H   OC.sub.2 H.sub.5                        CH.sub.3  Cl      H     H   H     H   Cl                                      CH.sub.3  NO.sub.2                                                                              H     H   H     H   Cl                                      CH.sub.3  F       H     H   H     F   CH.sub.2 OCH.sub.3                      CH.sub.3  F       H     H   H     H   SCH.sub.3                               CH.sub.3  H       H     H   H     H   CH.sub.2 OCH.sub.3                      CH.sub.3  CH.sub.3                                                                              H     H   NO.sub. 2                                                                           H   SCH.sub.3                               CH.sub.3  CF.sub.3                                                                              H     H   H     H   OCH.sub.2 CH.sub.2 OCH.sub.3            CH.sub.3  OC.sub.2 H.sub.5                                                                      H     H   OC.sub.2 H.sub.5                                                                    H   C.sub.2 H.sub.5                         CH.sub.3  SC.sub.2 H.sub.5                                                                      H     H   H     H   OC.sub.2 H.sub.5                        C.sub.2 H.sub.5                                                                         NO.sub.2                                                                              H     H   H     H   (CH.sub.3).sub.2 CHO                    C.sub.2 H.sub.5                                                                         Cl      H     H   H     H   OC.sub.2 H.sub.5                        C.sub.2 H.sub.5                                                                         Br      H     H   H     H   C.sub.2 H.sub.5                         C.sub.2 H.sub.5                                                                         OCH.sub.3                                                                             H     H   H     H   n-C.sub.3 H.sub.7 O                     C.sub.2 H.sub.5                                                                         CH.sub.3                                                                              H     H   CH.sub.3                                                                            H   CF.sub.3                                n-C.sub.3 H.sub.7                                                                       Cl      H     H   Cl    H   CF.sub.3                                n-C.sub.3 H.sub.7                                                                       OCH.sub.3                                                                             H     H   OCH.sub.3                                                                           H   Cl                                      n-C.sub.3 H.sub.7                                                                       F       H     H   F     H   OC.sub.2 H.sub.5                        CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                              H     H   H     H   OC.sub.2 H.sub.5                        CH.sub.3 (CH.sub.3).sub.2                                                               F       H     H   H     F   OCH.sub.2 CH.sub.2 OCH.sub.3            OCH.sub.3 F       H     H   H     H   C.sub.2 H.sub.5                         ______________________________________                                    

EXAMPLE 5N-[N-(4-methoxy-6-methylpyrimidin-2-yl)-N-methylaminocarbonyl]-2-thiophenesulfonamide

To a mixture, 1.5 g of 2-methylamino-4-methoxy-6-methylpyrimidine in 50ml of acetonitrile is added 1.9 g of 2-thiophenesulfonyl isocyanate.Filtration affordsN-[N-(4-methoxy-6-methylpyrimidin-2-yl)-N-methylaminocarbonyl]-2-thiophenesulfonamide.

By using equivalent amounts of an appropriate 2-alkylaminopyrimidine or2-alkylamino-1,3,5-triazine and 2-thiophenesulfonyl isocyanate, thecompounds of Formula I set forth in Table III can be prepared by theprocedure of Example 5.

                  TABLE III                                                       ______________________________________                                         ##STR27##                                                                        R.sub.1     Z        X           Y                                        ______________________________________                                        CH.sub.3    CH       CH.sub.3      CH.sub.3                                   CH.sub.3    CH       OCH.sub.3     CH.sub.3                                   CH.sub.3    CH       OCH.sub.3     OCH.sub.3                                  CH.sub.3    CH       CH.sub.2 CH.sub.3                                                                           OCH.sub.3                                  CH.sub.3    CH       OCH.sub.2 CH.sub.3                                                                          OCH.sub.3                                  CH.sub.3    CH       CF.sub.3      CH.sub.3                                   CH.sub.3    N        CH.sub.3      CH.sub.3                                   CH.sub.3    N        OCH.sub.3     CH.sub.3                                   CH.sub.3    N        OCH.sub.3     OCH                                        CH.sub.3    N        OCH.sub.2 CH.sub.3                                                                          OCH.sub.3                                  CH.sub.3    N        Cl            OCH.sub.3                                  CH.sub.3    N        SCH.sub.3     OCH.sub.3                                  C.sub.2 H.sub.5                                                                           CH       OCH.sub.3     CH.sub.3                                   C.sub.2 H.sub.5                                                                           CH       CH.sub.3      CH.sub.3                                   CH(CH.sub.3).sub.2                                                                        CH       OCH.sub.3     CH.sub.3                                   n-C.sub.3 H.sub.7                                                                         CH       CH.sub.3      CH.sub.3                                   C.sub.2 H.sub.5                                                                           N        OCH.sub.3     OCH.sub. 3                                 C.sub.2 H.sub.5                                                                           N        CH.sub.3      CH.sub.3                                   C.sub.2 H.sub.5                                                                           N        CH.sub.3      OCH.sub.3                                  n-C.sub.3 H.sub.7                                                                         N        OCH.sub.3     OCH.sub.3                                  CH(CH.sub.3).sub.2                                                                        N        OCH.sub.3     OCH.sub.3                                  n-C.sub.3 H.sub.7                                                                         N        CH.sub.3      CH.sub.3                                   CH.sub.3    CH       Cl            CH.sub.3                                   CH.sub.3    CH       Cl            OCH.sub.3                                  C.sub.2 H.sub.5                                                                           CH       n-C.sub.3 H.sub.7 O                                                                         CH.sub.3                                   C.sub.2 H.sub.5                                                                           CH       OCH(CH.sub.3).sub.2                                                                         OCH.sub.3                                  C.sub.2 H.sub.5                                                                           CH       SCH.sub.3     CH.sub.3                                   CH.sub.3    N        n-C.sub.3 H.sub.7 O                                                                         OCH.sub.3                                  CH.sub.3    N        OCH.sub.2 CH.sub.2 OCH.sub.3                                                                OCH.sub.3                                  CH.sub.3    N        C.sub.2 H.sub.5                                                                             CH.sub.3                                   CH.sub.3    N        OCH(CH.sub.3).sub.2                                                                         CH.sub.3                                   ______________________________________                                    

EXAMPLE 6N-[N-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-N-aminocarbonyl]-2,5-dimethoxy-N-methylbenzenesulfonamide

An equivalent amount of sodium hydride (50% mineral oil dispersion) isadded to a solution ofN-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]2,5-dimethoxybenzenesulfonamidein dimethylformamide under a nitrogen atmosphere. After hydrogenevolution ceases, an equivalent amount of dimethyl sulfate is added.After stirring for 2-18 hours, the reaction mixture is poured into alarge volume of water. The resulting precipitate is filtered to yieldN-[N-(4,6-dimethoxy-1,3,5-triazin-2-yl)-N-aminocarbonyl]-2,5-dimethoxy-N-methylbenzenesulfonamide.

EXAMPLE 7N-[N-(4-Methoxy-6-methylpyrimidin-2-yl)-N-methylaminocarbonyl]2,5-dichloro-N-methylbenzenesulfonamide

To 3.0 g of N-[(2,5-dichlorophenyl)sulfonyl]-N-methylcarbamyl chloridein 50 ml of tetrahydrofuran containing 1.0 g of triethylamine is added1.5 g of 2-methylamino-4-methoxy-6-methylpyrimidine. After stirring atreflux for several hours, the precipitated salts are filtered off andthe filtrate is concentrated to yieldN-[N-(4-methoxy-6-methylpyrimidin-2-yl)-N-methylaminocarbonyl]2,5-dichloro-N-methylbenzenesulfonamide.

By using an appropriateN-(1,3,5-triazin-2-yl)-N-aminocarbonylbenzenesulfonamide orN-pyrimidin-2-yl-N-aminocarbonylbenzenesulfonamide, the followingcompounds of Formula I as set forth in Table IV can be prepared by theprocedure of Example 6. Alternatively, by using an appopriatelysubstituted sulfonyl-N-alkylbenzene carbamyl chloride and an appropriate2-aminopyrimidine or 2-amino-1,3,5-triazine, the same compounds ofFormula I can be prepared by the procedure of Example 7.

                  TABLE IV-A                                                      ______________________________________                                         ##STR28##                                                                      R.sub.1   R.sub.2   R.sub.4                                                                             R.sub.5                                                                             R.sub.6                                                                            R.sub.7                                                                             R.sub.8                          ______________________________________                                        H       CH.sub.3  OCH.sub.3                                                                             H     H    OCH.sub.3                                                                           H                                  H       CH.sub.3  Cl      H     H    H     H                                  H       CH.sub.3  NO.sub.2                                                                              H     H    H     H                                  H       CH.sub.3  Cl      H     H    Cl    H                                  H       CH.sub.3  CH.sub.3                                                                              H     H    H     H                                  H       CH.sub.3  Cl      H     F    H     H                                  H       CH.sub.3  H       H     H    H     H                                  H       CH.sub.3  CH.sub.3                                                                              H     H    CH.sub.3                                                                            H                                  H       CH.sub.3  OC.sub.2 H.sub.5                                                                      H     H    OC.sub.2 H.sub.5                                                                    H                                  CH.sub.3                                                                              CH.sub.3  Cl      H     H    H     H                                  CH.sub.3                                                                              CH.sub.3  NO.sub.2                                                                              H     H    CH.sub.3                                                                            H                                  CH.sub.3                                                                              CH.sub.3  CH.sub.3                                                                              H     H    NO.sub.2                                                                            H                                  CH.sub.3                                                                              CH.sub.3  Cl      H     H    Cl    H                                  CH.sub.3                                                                              CH.sub.3  CH.sub.3                                                                              H     H    Cl    H                                  CH.sub.3                                                                              CH.sub.3  CH.sub.3                                                                              CH.sub.3                                                                            H    CH.sub.3                                                                            CH.sub.3                           CH.sub.3                                                                              CH.sub.3  OCH.sub.3                                                                             H     H    OCH.sub.3                                                                           H                                  CH.sub.3                                                                              CH.sub.3  F       H     H    F     H                                  C.sub.2 H.sub.5                                                                       CH.sub.3  NO.sub.2                                                                              H     H    H     H                                  C.sub.2 H.sub.5                                                                       CH.sub.3  Cl      H     H    H     Cl                                 H       C.sub.2 H.sub.5                                                                         F       H     H    H     H                                  H       C.sub.2 H.sub.5                                                                         CF.sub.3                                                                              H     H    H     H                                  H       C.sub.2 H.sub.5                                                                         OCH.sub.3                                                                             H     H    OCH.sub.3                                                                           H                                  CH.sub.3                                                                              C.sub.2 H.sub.5                                                                         Cl      H     H    H     H                                  CH.sub.3                                                                              C.sub.2 H.sub.5                                                                         NO.sub.2                                                                              H     H    Cl    H                                  CH.sub.3                                                                              C.sub.2 H.sub.5                                                                         CH.sub.3                                                                              CH.sub.3                                                                            H    CH.sub.3                                                                            CH.sub.3                           n-C.sub.3 H.sub.7                                                                     C.sub.2 H.sub.5                                                                         F       H     H    H     F                                  n-C.sub.3 H.sub.7                                                                     C.sub.2 H.sub.5                                                                         Br      H     H    H     H                                  n-C.sub.3 H.sub.7                                                                     C.sub.2 H.sub.5                                                                         CF.sub.3                                                                              H     H    H     H                                  CH(CH.sub.3).sub.2                                                                    CH.sub.3  Cl      H     H    Cl    H                                  CH.sub.3                                                                              n-C.sub.3 H.sub.7                                                                       Cl      H     H    Cl    H                                  H       n-C.sub.3 H.sub.7                                                                       NO.sub.2                                                                              H     H    H     H                                  H       CH(CH.sub.3).sub.2                                                                      CF.sub.3                                                                              H     H    H     H                                  CH.sub.3                                                                              CH(CH.sub.3).sub.2                                                                      Cl      H     H    H     H                                  OCH.sub.3                                                                             CH.sub.3  Cl      H     H    H     H                                  OCH.sub.3                                                                             CH.sub.3  CH.sub.3                                                                              H     H    H     H                                  ______________________________________                                    

                  TABLE IV-B                                                      ______________________________________                                         ##STR29##                                                                      R.sub.1   R.sub.2   R.sub.4                                                                             R.sub.5                                                                             R.sub.6                                                                            R.sub.7                                                                             R.sub.8                          ______________________________________                                        H       CH.sub.3  OCH.sub.3                                                                             H     H    OCH.sub.3                                                                           H                                  H       CH.sub.3  Cl      H     H    H     H                                  H       CH.sub.3  NO.sub.2                                                                              H     H    H     H                                  H       CH.sub.3  Cl      H     H    Cl    H                                  H       CH.sub.3  CH.sub.3                                                                              H     H    H     H                                  H       CH.sub.3  Cl      H     F    H     H                                  H       CH.sub.3  H       H     H    H     H                                  H       CH.sub.3  CH.sub.3                                                                              H     H    CH.sub.3                                                                            H                                  H       CH.sub.3  OC.sub.2 H.sub.5                                                                      H     H    OC.sub.2 H.sub.5                                                                    H                                  CH.sub.3                                                                              CH.sub.3  NO.sub.2                                                                              H     H    CH.sub.3                                                                            H                                  CH.sub.3                                                                              CH.sub.3  Cl      H     H    Cl    H                                  CH.sub.3                                                                              CH.sub.3  CH.sub.3                                                                              H     H    Cl    H                                  CH.sub.3                                                                              CH.sub.3  CH.sub.3                                                                              CH.sub.3                                                                            H    CH.sub.3                                                                            CH.sub.3                           CH.sub.3                                                                              CH.sub.3  OCH.sub.3                                                                             H     H    H     H                                  CH.sub.3                                                                              CH.sub.3  F       H     H    F     H                                  C.sub.2 H.sub.5                                                                       CH.sub.3  NO.sub.2                                                                              H     H    H     H                                  C.sub.2 H.sub.5                                                                       CH.sub.3  Cl      H     H    H     Cl                                 H       C.sub.2 H.sub.5                                                                         F       H     H    H     H                                  H       C.sub.2 H.sub.5                                                                         CF.sub.3                                                                              H     H    H     H                                  H       C.sub.2 H.sub.5                                                                         OC.sub.2 H.sub.5                                                                      H     H    H     H                                  CH.sub.3                                                                              C.sub.2 H.sub.5                                                                         OCH.sub.3                                                                             H     H    OCH.sub.3                                                                           H                                  CH.sub.3                                                                              C.sub.2 H.sub.5                                                                         CH.sub.3                                                                              H     H    NO.sub.2                                                                            H                                  n-C.sub.3 H.sub.7                                                                     C.sub.2 H.sub.5                                                                         F       H     H    H     F                                  n-C.sub.3 H.sub.7                                                                     C.sub.2 H.sub.5                                                                         Br      H     H    H     H                                  CH(CH.sub.3).sub.2                                                                    C.sub.2 H.sub.5                                                                         CF.sub.3                                                                              H     H    H     H                                  CH(CH.sub.3).sub.2                                                                    CH.sub.3  Cl      H     H    OCH.sub.3                                                                           H                                  n-C.sub.3 H.sub.7                                                                     CH.sub.3  F       H     H    F     H                                  CH.sub.3                                                                              n-C.sub.3 H.sub.7                                                                       Cl      H     H    Cl    H                                  H       n-C.sub.3 H.sub.7                                                                       NO.sub.2                                                                              H     H    H     H                                  H       CH(CH.sub.3).sub.2                                                                      CF.sub.3                                                                              H     H    H     H                                  CH.sub.3                                                                              CH(CH.sub.3).sub.2                                                                      Cl      H     H    H     H                                  OCH.sub.3                                                                             CH.sub.3  F       H     H    H     F                                  OCH.sub.3                                                                             CH.sub.3  CH.sub.3                                                                              H     H    H     H                                  ______________________________________                                    

                  TABLE IV-C                                                      ______________________________________                                         ##STR30##                                                                      R.sub.1   R.sub.2   R.sub.4                                                                             R.sub.5                                                                             R.sub.6                                                                            R.sub.7                                                                             R.sub.8                          ______________________________________                                        H       CH.sub.3  OCH.sub.3                                                                             H     H    OCH.sub.3                                                                           H                                  H       CH.sub.3  Cl      H     H    H     H                                  H       CH.sub.3  NO.sub.2                                                                              H     H    H     H                                  H       CH.sub.3  Cl      H     H    Cl    H                                  H       CH.sub.3  CH.sub.3                                                                              H     H    H     H                                  H       CH.sub.3  Cl      H     F    H     H                                  H       CH.sub.3  H       H     H    H     H                                  H       CH.sub.3  CH.sub.3                                                                              H     H    CH.sub.3                                                                            H                                  H       CH.sub.3  OC.sub.2 H.sub.5                                                                      H     H    OC.sub.2 H.sub.5                                                                    H                                  CH.sub.3                                                                              CH.sub.3  NO.sub.2                                                                              H     H    CH.sub.3                                                                            H                                  CH.sub.3                                                                              CH.sub.3  Cl      H     H    Cl    H                                  CH.sub.3                                                                              CH.sub.3  CH.sub.3                                                                              H     H    Cl    H                                  CH.sub.3                                                                              CH.sub.3  CH.sub.3                                                                              CH.sub.3                                                                            H    CH.sub.3                                                                            CH.sub.3                           CH.sub.3                                                                              CH.sub.3  OCH.sub.3                                                                             H     H    H     H                                  CH.sub.3                                                                              CH.sub.3  F       H     H    F     H                                  C.sub.2 H.sub.5                                                                       CH.sub.3  NO.sub.2                                                                              H     H    H     H                                  C.sub.2 H.sub.5                                                                       CH.sub.3  Cl      H     H    H     Cl                                 H       C.sub.2 H.sub.5                                                                         F       H     H    H     H                                  H       C.sub.2 H.sub.5                                                                         CF.sub.3                                                                              H     H    H     H                                  H       C.sub.2 H.sub.5                                                                         OC.sub.2 H.sub.5                                                                      H     H    H     H                                  CH.sub.3                                                                              C.sub.2 H.sub.5                                                                         OCH.sub.3                                                                             H     H    OCH.sub.3                                                                           H                                  CH.sub.3                                                                              C.sub.2 H.sub.5                                                                         CH.sub.3                                                                              H     H    NO.sub.2                                                                            H                                  n-C.sub.3 H.sub.7                                                                     C.sub.2 H.sub.5                                                                         F       H     H    H     F                                  n-C.sub.3 H.sub.7                                                                     C.sub.2 H.sub.5                                                                         Br      H     H    H     H                                  CH(CH.sub.3).sub.2                                                                    C.sub.2 H.sub.5                                                                         CF.sub.3                                                                              H     H    H     H                                  CH(CH.sub.3).sub.2                                                                    CH.sub.3  Cl      H     H    OCH.sub.3                                                                           H                                  n-C.sub.3 H.sub.7                                                                     CH.sub.3  F       H     H    F     H                                  OCH.sub.3                                                                             CH.sub.3  CH.sub.3                                                                              H     H    H     H                                  OCH.sub.3                                                                             CH.sub.3  Cl      H     H    H     H                                  CH.sub.3                                                                              n-C.sub.3 H.sub.7                                                                       Cl      H     H    Cl    H                                  H       n-C.sub.3 H.sub.7                                                                       NO.sub.2                                                                              H     H    H     H                                  H       CH(CH.sub.3).sub.2                                                                      CF.sub.3                                                                              H     H    H     H                                  CH.sub.3                                                                              CH(CH.sub.3).sub.2                                                                      Cl      H     H    H     H                                  ______________________________________                                    

                                      TABLE IV-D                                  __________________________________________________________________________     ##STR31##                                                                    R.sub.1                                                                             R.sub.2                                                                             R.sub.4                                                                            R.sub.5                                                                         R.sub.6                                                                         R.sub.7                                                                            R.sub.8                                                                         X                                                 __________________________________________________________________________    H     CH.sub.3                                                                            Cl   H H H    H C.sub.2 H.sub.5                                   H     CH.sub.3                                                                            NO.sub.2                                                                           H H H    H C.sub.2 H.sub.5                                   H     CH.sub.3                                                                            CH.sub.3                                                                           H H H    H C.sub.2 H.sub.5                                   H     CH.sub.3                                                                            Cl   H H NO.sub.2                                                                           H OC.sub.2 H.sub.5                                  H     CH.sub.3                                                                            NO.sub.2                                                                           H H CH.sub.3                                                                           H OC.sub.2 H.sub.5                                  H     CH.sub.3                                                                            CH.sub.3                                                                           H H H    H n-C.sub.3 H.sub.7 O                               H     CH.sub.3                                                                            OCH.sub.3                                                                          H H H    H SCH.sub. 3                                        H     C.sub.2 H.sub.5                                                                     Cl   H H Cl   H CH.sub.2 OCH.sub.3                                CH.sub.3                                                                            CH.sub.3                                                                            F    H H H    H C.sub.2 H.sub.5                                   CH.sub.3                                                                            CH.sub.3                                                                            CF.sub.3                                                                           H H H    H C.sub.2 H.sub.5                                   CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                           H H CH.sub.3                                                                           H OC.sub.2 H.sub.5                                  CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                           H H NO.sub.2                                                                           H OC.sub.2 H.sub.5                                  CH.sub.3                                                                            CH.sub.3                                                                            H    H H H    H CF.sub.3                                          C.sub.2 H.sub.5                                                                     CH.sub.3                                                                            F    H H F    H OCH.sub.2 CH.sub.2 OCH.sub.3                      C.sub.2 H.sub.5                                                                     CH.sub.3                                                                            Br   H H H    H n-C.sub.3 H.sub.7 O                               C.sub.2 H.sub.5                                                                     CH.sub.3                                                                            OCH.sub.3                                                                          H H OCH.sub.3                                                                          H Cl                                                CH.sub.3                                                                            C.sub.2 H.sub.5                                                                     Cl   H F H    H OC.sub.2 H.sub.5                                  C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                                                                     NO.sub.2                                                                           H H CH.sub.3                                                                           H CH.sub.2 OCH.sub.3                                n-C.sub.3 H.sub.7                                                                   CH.sub.3                                                                            Cl   H H H    Cl                                                                              SCH.sub.3                                         n-C.sub.3 H.sub.7                                                                   CH.sub.3                                                                            OCH.sub.3                                                                          H H Cl   H OC.sub.2 H.sub.5                                  OCH.sub.3                                                                           CH.sub.3                                                                            F    H H H    F OCH(CH.sub.3).sub.2                               CH(CH.sub.3).sub.2                                                                  C.sub.2 H.sub.5                                                                     Cl   H H NO.sub.2                                                                           H C.sub.2 H.sub.5                                   CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                   Cl   H H Cl   H OC.sub.2 H.sub.5                                  H     n-C.sub.3 H.sub.7                                                                   NO.sub.2                                                                           H H H    H OC.sub.2 H.sub.5                                  H     CH(CH.sub.3).sub.2                                                                  CF.sub.3                                                                           H H H    H OC.sub.2 H.sub.5                                  CH.sub.3                                                                            CH(CH.sub.3).sub.2                                                                  Cl   H H H    H OC.sub.2 H.sub.5                                  __________________________________________________________________________

                                      TABLE IV-E                                  __________________________________________________________________________     ##STR32##                                                                    R.sub.1                                                                             R.sub.2                                                                              R.sub.4                                                                           R.sub.5                                                                          R.sub.6                                                                         R.sub.7                                                                            R.sub.8                                                                         X                                                __________________________________________________________________________    H     CH.sub.3                                                                             Cl  H  H H    H C.sub.2 H.sub.5                                  H     CH.sub.3                                                                             NO.sub.2                                                                          H  H H    H C.sub.2 H.sub.5                                  H     CH.sub.3                                                                             CH.sub.3                                                                          H  H H    H C.sub.2 H.sub.5                                  H     CH.sub.3                                                                             Cl  H  H NO.sub.2                                                                           H OC.sub.2 H.sub.5                                 H     CH.sub.3                                                                             NO.sub.2                                                                          H  H CH.sub.3                                                                           H OC.sub.2 H.sub.5                                 H     CH.sub.3                                                                             CH.sub.3                                                                          H  H H    H n-C.sub.3 H.sub.7 O                              H     CH.sub.3                                                                             OCH.sub. 3                                                                        H  H H    H SCH.sub.3                                        H     C.sub.2 H.sub.5                                                                      Cl  H  H Cl   H CH.sub.2 OCH.sub.3                               CH.sub.3                                                                            CH.sub.3                                                                             F   H  H H    H C.sub.2 H.sub.5                                  CH.sub.3                                                                            CH.sub.3                                                                             CF.sub.3                                                                          H  H H    H C.sub.2 H.sub.5                                  CH.sub.3                                                                            CH.sub.3                                                                             CH.sub.3                                                                          H  H CH.sub.3                                                                           H OC.sub.2 H.sub.5                                 CH.sub.3                                                                            CH.sub.3                                                                             CH.sub.3                                                                          H  H NO.sub.2                                                                           H OC.sub.2 H.sub.5                                 CH.sub.3                                                                            CH.sub.3                                                                             H   H  H H    H CF.sub.3                                         C.sub.2 H.sub.5                                                                     CH.sub.3                                                                             F   H  H F    H OCH.sub.2 CH.sub.2 OCH.sub.3                     C.sub.2 H.sub.5                                                                     CH.sub.3                                                                             Br  H  H H    H n-C.sub.3 H.sub.7 O                              C.sub.2 H.sub.5                                                                     CH.sub.3                                                                             OCH.sub.3                                                                         H  H OCH.sub.3                                                                          H Cl                                               CH.sub.3                                                                            C.sub.2 H.sub.5                                                                      Cl  H  F H    H OC.sub.2 H.sub.5                                 C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                                                                      NO.sub.2                                                                          H  H CH.sub.3                                                                           H CH.sub.2 OCH.sub.3                               n-C.sub.3 H.sub.7                                                                   CH.sub.3                                                                             Cl  H  H H    Cl                                                                              SCH.sub.3                                        n-C.sub.3 H.sub.7                                                                   CH.sub.3                                                                             OCH.sub.3                                                                         H  H Cl   H OC.sub.2 H.sub.5                                 CH(CH.sub. 3).sub.2                                                                 CH.sub.3                                                                             F   H  H H    F OCH(CH.sub.3).sub.2                              CH(CH.sub.3).sub.2                                                                  CH.sub.3                                                                             Cl  H  H NO.sub.2                                                                           H C.sub.2 H.sub.5                                  OCH.sub.3                                                                           CH.sub.3                                                                             Br  H  H H    H OC.sub.2 H.sub.5                                 CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                    Cl  H  H Cl   H OC.sub.2 H.sub.5                                 H     n-C.sub.3 H.sub.7                                                                    NO.sub.2                                                                          H  H H    H OC.sub.2 H.sub.5                                 H     CH(CH.sub.3).sub.2                                                                   CF.sub.3                                                                          H  H H    H OC.sub.2 H.sub.5                                 CH.sub.3                                                                            CH(CH.sub.3).sub.2                                                                   Cl  H  H H    H OC.sub.2 H.sub.5                                 __________________________________________________________________________

                  TABLE IV-F                                                      ______________________________________                                         ##STR33##                                                                      R.sub.1   R.sub.2    R.sub.4                                                                             R.sub.5                                                                             R.sub.6                                                                           R.sub.7                                                                              R.sub.8                         ______________________________________                                        H       CH.sub.3   OCH.sub.3                                                                             H     H   OCH.sub.3                                                                            H                                 H       CH.sub.3   Cl      H     H   H      H                                 H       CH.sub.3   NO.sub.2                                                                              H     H   H      H                                 H       CH.sub.3   Cl      H     H   Cl     H                                 H       CH.sub.3   CH.sub.3                                                                              H     H   H      H                                 H       CH.sub.3   Cl      H     F   H      H                                 H       CH.sub.3   H       H     H   H      H                                 H       CH.sub.3   CH.sub.3                                                                              H     H   CH.sub.3                                                                             H                                 H       CH.sub.3   OC.sub.2 H.sub.5                                                                      H     H   OC.sub.2 H.sub.5                                                                     H                                 CH.sub.3                                                                              CH.sub.3   NO.sub.2                                                                              H     H   CH.sub.3                                                                             H                                 CH.sub.3                                                                              CH.sub.3   Cl      H     H   Cl     H                                 CH.sub.3                                                                              CH.sub.3   CH.sub.3                                                                              H     H   Cl     H                                 CH.sub.3                                                                              CH.sub.3   CH.sub.3                                                                              CH.sub.3                                                                            H   CH.sub.3                                                                             CH.sub.3                          CH.sub.3                                                                              CH.sub.3   OCH.sub.3                                                                             H     H   H      H                                 CH.sub.3                                                                              CH.sub.3   F       H     H   F      H                                 C.sub.2 H.sub.5                                                                       CH.sub.3   NO.sub.2                                                                              H     H   H      H                                 C.sub.2 H.sub.5                                                                       CH.sub.3   Cl      H     H   H      Cl                                H       C.sub.2 H.sub.5                                                                          F       H     H   H      H                                 H       C.sub.2 H.sub.5                                                                          CF.sub.3                                                                              H     H   H      H                                 H       C.sub.2 H.sub.5                                                                          OC.sub.2 H.sub.5                                                                      H     H   H      H                                 CH.sub.3                                                                              C.sub.2 H.sub.5                                                                          OCH.sub.3                                                                             H     H   OCH.sub.3                                                                            H                                 CH.sub.3                                                                              C.sub.2 H.sub.5                                                                          CH.sub.3                                                                              H     H   NO.sub.2                                                                             H                                 n-C.sub.3 H.sub.7                                                                     C.sub.2 H.sub.5                                                                          F       H     H   H      F                                 n-C.sub.3 H.sub.7                                                                     C.sub.2 H.sub.5                                                                          Br      H     H   H      H                                 CH(CH.sub.3).sub.2                                                                    C.sub.2 H.sub.5                                                                          CF.sub.3                                                                              H     H   H      H                                 CH(CH.sub.3).sub.2                                                                    CH.sub.3   Cl      H     H   OCH.sub.3                                                                            H                                 n-C.sub.3 H.sub.7                                                                     CH.sub.3   F       H     H   F      H                                 OCH.sub.3                                                                             CH.sub.3   CH.sub.3                                                                              H     H   H      H                                 OCH.sub.3                                                                             CH.sub.3   Cl      H     H   H      H                                 CH.sub.3                                                                              n-C.sub.3 H.sub.7                                                                        Cl      H     H   Cl     H                                 H       n-C.sub.3 H.sub.7                                                                        NO.sub.2                                                                              H     H   H      H                                 H       CH(CH.sub.3).sub.2                                                                       CF.sub.3                                                                              H     H   H      H                                 CH.sub.3                                                                              CH(CH.sub.3).sub.2                                                                       Cl      H     H   H      Cl                                ______________________________________                                    

                  TABLE IV-G                                                      ______________________________________                                         ##STR34##                                                                      R.sub.1   R.sub.2    R.sub.4                                                                             R.sub.5                                                                             R.sub.6                                                                           R.sub.7                                                                              R.sub.8                         ______________________________________                                        H       CH.sub.3   Cl      H     H   H      H                                 H       CH.sub.3   NO.sub.2                                                                              H     H   H      H                                 H       CH.sub.3   OCH.sub.3                                                                             H     H   OCH.sub.3                                                                            H                                 H       CH.sub.3   CH.sub.3                                                                              H     H   H      H                                 H       CH.sub.3   H       H     H   H      H                                 CH.sub.3                                                                              CH.sub.3   NO.sub.2                                                                              H     H   CH.sub.3                                                                             H                                 CH.sub.3                                                                              CH.sub.3   Cl      H     H   Cl     H                                 H       CH.sub.3   Cl      H     F   H      H                                 H       CH.sub.3   OC.sub.2 H.sub.5                                                                      H     H   OC.sub.2 H.sub.5                                                                     H                                 H       CH.sub.3   H       F     H   H      H                                 CH.sub.3                                                                              CH.sub.3   CH.sub.3                                                                              H     H   Cl     H                                 CH.sub.3                                                                              CH.sub.3   CH.sub.3                                                                              CH.sub.3                                                                            H   CH.sub.3                                                                             CH.sub.3                          CH.sub.3                                                                              CH.sub.3   OCH.sub.3                                                                             H     H   H      H                                 CH.sub.3                                                                              CH.sub.3   F       H     H   F      H                                 C.sub.2 H.sub.5                                                                       CH.sub.3   NO.sub.2                                                                              H     H   H      H                                 C.sub.2 H.sub.5                                                                       CH.sub.3   Cl      H     H   H      Cl                                H       C.sub.2 H.sub.5                                                                          F       H     H   H      H                                 H       C.sub.2 H.sub.5                                                                          CF.sub.3                                                                              H     H   H      H                                 H       C.sub.2 H.sub.5                                                                          OC.sub.2 H.sub.5                                                                      H     H   H      H                                 CH.sub.3                                                                              C.sub.2 H.sub.5                                                                          OCH.sub.3                                                                             H     H   OCH.sub.3                                                                            H                                 CH.sub.3                                                                              C.sub.2 H.sub.5                                                                          CH.sub.3                                                                              H     H   NO.sub.2                                                                             H                                 n-C.sub.3 H.sub.7                                                                     C.sub.2 H.sub.5                                                                          F       H     H   H      F                                 n-C.sub.3 H.sub.7                                                                     C.sub.2 H.sub.5                                                                          Br      H     H   H      H                                 CH(CH.sub.3).sub.2                                                                    C.sub.2 H.sub.5                                                                          CF.sub.3                                                                              H     H   H      H                                 CH(CH.sub.3).sub.2                                                                    CH.sub.3   Cl      H     H   OCH.sub.3                                                                            H                                 n-C.sub.3 H.sub.7                                                                     CH.sub.3   F       H     H   F      H                                 OCH.sub.3                                                                             CH.sub.3   CH.sub.3                                                                              H     H   H      H                                 OCH.sub.3                                                                             CH.sub.3   Cl      H     H   H      H                                 CH.sub.3                                                                              n-C.sub.3 H.sub.7                                                                        Cl      H     H   Cl     H                                 H       n-C.sub.3 H.sub.7                                                                        NO.sub.2                                                                              H     H   H      H                                 H       CH(CH.sub.3).sub.2                                                                       CF.sub.3                                                                              H     H   H      H                                 CH.sub.3                                                                              CH(CH.sub.3).sub.2                                                                       Cl      H     H   H      Cl                                ______________________________________                                    

                  TABLE IV-H                                                      ______________________________________                                         ##STR35##                                                                      R.sub.1   R.sub.2    R.sub.4                                                                             R.sub.5                                                                             R.sub.6                                                                           R.sub.7                                                                              R.sub.8                         ______________________________________                                        H       CH.sub.3   NO.sub.2                                                                              H     H   H      H                                 H       CH.sub.3   Cl      H     H   H      H                                 H       CH.sub.3   CH.sub.3                                                                              H     H   H      H                                 H       CH.sub.3   OCH.sub.3                                                                             H     H   OCH.sub.3                                                                            H                                 H       CH.sub.3   OC.sub.2 H.sub.5                                                                      H     H   OC.sub.2 H.sub.5                                                                     H                                 H       CH.sub.3   Cl      H     H   H      Cl                                H       CH.sub.3   Cl      H     H   NO.sub.2                                                                             H                                 H       CH.sub.3   H       H     H   H      H                                 H       CH.sub.3   OCH.sub.3                                                                             H     H   H      H                                 CH.sub.3                                                                              CH.sub.3   Cl      H     H   Cl     H                                 CH.sub.3                                                                              CH.sub.3   NO.sub.2                                                                              H     H   CH.sub.3                                                                             H                                 CH.sub.3                                                                              CH.sub.3   CH.sub.3                                                                              H     H   Cl     H                                 CH.sub.3                                                                              CH.sub.3   CH.sub.3                                                                              CH.sub.3                                                                            H   CH.sub.3                                                                             CH.sub.3                          CH.sub.3                                                                              CH.sub.3   OCH.sub.3                                                                             H     H   H      H                                 CH.sub.3                                                                              CH.sub.3   F       H     H   F      H                                 C.sub.2 H.sub.5                                                                       CH.sub.3   NO.sub.2                                                                              H     H   H      H                                 C.sub.2 H.sub.5                                                                       CH.sub.3   Cl      H     H   H      Cl                                H       C.sub.2 H.sub.5                                                                          F       H     H   H      H                                 H       C.sub.2 H.sub.5                                                                          CF.sub.3                                                                              H     H   H      H                                 H       C.sub.2 H.sub.5                                                                          OC.sub.2 H.sub.5                                                                      H     H   H      H                                 CH.sub.3                                                                              C.sub.2 H.sub.5                                                                          CH.sub.3                                                                              H     H   NO.sub.2                                                                             H                                 CH.sub.3                                                                              C.sub.2 H.sub.5                                                                          OCH.sub.3                                                                             H     H   OCH.sub.3                                                                            H                                 n-C.sub.3 H.sub.7                                                                     C.sub.2 H.sub.5                                                                          F       H     H   H      F                                 n-C.sub.3 H.sub.7                                                                     C.sub.2 H.sub.5                                                                          Br      H     H   H      H                                 CH(CH.sub.3).sub.2                                                                    C.sub.2 H.sub.5                                                                          CF.sub.3                                                                              H     H   H      H                                 CH(CH.sub.3).sub.2                                                                    CH.sub.3   Cl      H     H   OCH.sub.3                                                                            H                                 n-C.sub.3 H.sub.7                                                                     CH.sub.3   F       H     H   F      H                                 OCH.sub.3                                                                             CH.sub.3   CH.sub.3                                                                              H     H   H      H                                 OCH.sub.3                                                                             CH.sub.3   Cl      H     H   H      H                                 CH.sub.3                                                                              n-C.sub.3 H.sub.7                                                                        Cl      H     H   Cl     H                                 H       n-C.sub.3 H.sub.7                                                                        NO.sub.2                                                                              H     H   H      H                                 H       CH(CH.sub.3).sub.2                                                                       CF.sub.3                                                                              H     H   H      H                                 CH.sub.3                                                                              CH(CH.sub.3).sub.2                                                                       Cl      H     H   H      Cl                                ______________________________________                                    

                                      TABLE IV-I                                  __________________________________________________________________________     ##STR36##                                                                    R.sub.1                                                                             R.sub.2                                                                              R.sub.4                                                                           R.sub.5                                                                          R.sub.6                                                                         R.sub.7                                                                           R.sub.8                                                                         X                                                 __________________________________________________________________________    H     CH.sub.3                                                                             Cl  H  H H   H C.sub.2 H.sub.5                                   H     CH.sub.3                                                                             NO.sub.2                                                                          H  H H   H C.sub.2 H.sub.5                                   H     CH.sub.3                                                                             CH.sub.3                                                                          H  H H   H C.sub.2 H.sub.5                                   H     CH.sub.3                                                                             Cl  H  H NO.sub.2                                                                          H OC.sub.2 H.sub.5                                  H     CH.sub.3                                                                             NO.sub.2                                                                          H  H CH.sub.3                                                                          H OC.sub.2 H.sub.5                                  H     CH.sub.3                                                                             CH.sub.3                                                                          H  H H   H n-C.sub.3 H.sub.7 O                               H     CH.sub.3                                                                             OCH.sub.3                                                                         H  H H   H SCH.sub.3                                         H     C.sub.2 H.sub.5                                                                      Cl  H  H Cl  H CH.sub.2 OCH.sub.3                                CH.sub.3                                                                            CH.sub.3                                                                             F   H  H H   H C.sub.2 H.sub.5                                   CH.sub.3                                                                            CH.sub.3                                                                             CF.sub.3                                                                          H  H H   H C.sub.2 H.sub.5                                   CH.sub.3                                                                            CH.sub.3                                                                             CH.sub.3                                                                          H  H CH.sub.3                                                                          H OC.sub.2 H.sub.5                                  CH.sub.3                                                                            CH.sub.3                                                                             CH.sub.3                                                                          H  H NO.sub.2                                                                          H OC.sub.2 H.sub.5                                  CH.sub.3                                                                            CH.sub.3                                                                             H   H  H H   H CF.sub.3                                          C.sub.2 H.sub.5                                                                     CH.sub.3                                                                             F   H  H F   H OCH.sub.2 CH.sub.2 OCH.sub.3                      C.sub.2 H.sub.5                                                                     CH.sub.3                                                                             Br  H  H H   H n-C.sub.3 H.sub.7 O                               C.sub.2 H.sub.5                                                                     CH.sub.3                                                                             OCH.sub.3                                                                         H  H OCH.sub.3                                                                         H Cl                                                CH.sub.3                                                                            C.sub.2 H.sub.5                                                                      Cl  H  F H   H OC.sub.2 H.sub.5                                  C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                                                                      NO.sub.2                                                                          H  H CH.sub.3                                                                          H CH.sub.2 OCH.sub.3                                n-C.sub.3 H.sub.7                                                                   CH.sub.3                                                                             Cl  H  H H   Cl                                                                              SCH.sub.3                                         n-C.sub.3 H.sub.7                                                                   CH.sub.3                                                                             OCH.sub.3                                                                         H  H Cl  H OC.sub.2 H.sub.5                                  OCH.sub.3                                                                           CH.sub.3                                                                             F   H  H H   F OCH(CH.sub.3).sub.2                               CH(CH.sub.3).sub.2                                                                  CH.sub.3                                                                             Cl  H  H NO.sub.2                                                                          H C.sub.2 H.sub.5                                   CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                    Cl  H  H Cl  H OC.sub.2 H.sub.5                                  H     n-C.sub.3 H.sub.7                                                                    NO.sub.2                                                                          H  H H   H OC.sub.2 H.sub.5                                  H     CH(CH.sub.3).sub.2                                                                   CF.sub.3                                                                          H  H H   H OC.sub.2 H.sub.5                                  CH.sub.3                                                                            CH(CH.sub.3).sub.2                                                                   Cl  H  H H   H OC.sub.2 H.sub.5                                  __________________________________________________________________________

                                      TABLE IV-J                                  __________________________________________________________________________       STR37##                                                                    R.sub.1                                                                             R.sub.2                                                                              R.sub.4                                                                           R.sub.5                                                                          R.sub.6                                                                         R.sub.7                                                                            R.sub.8                                                                         X                                                __________________________________________________________________________    H     CH.sub.3                                                                             Cl  H  H H    H C.sub.2 H.sub.5                                  H     CH.sub.3                                                                             NO.sub.2                                                                          H  H H    H C.sub.2 H.sub.5                                  H     CH.sub.3                                                                             CH.sub.3                                                                          H  H H    H C.sub.2 H.sub.5                                  H     CH.sub.3                                                                             Cl  H  H NO.sub.2                                                                           H OC.sub.2 H.sub.5                                 H     CH.sub.3                                                                             NO.sub.2                                                                          H  H CH.sub.3                                                                           H OC.sub.2 H.sub.5                                 H     CH.sub.3                                                                             CH.sub.3                                                                          H  H H    H n-C.sub.3 H.sub.7 O                              H     CH.sub.3                                                                             OCH.sub.3                                                                         H  H H    H SCH.sub.3                                        H     CH.sub. 3                                                                            Cl  H  H Cl   H CH.sub.2 OCH.sub.3                               CH.sub.3                                                                            CH.sub.3                                                                             F   H  H H    H C.sub.2 H.sub.5                                  CH.sub.3                                                                            CH.sub.3                                                                             CF.sub.3                                                                          H  H H    H C.sub.2 H.sub.5                                  CH.sub.3                                                                            CH.sub.3                                                                             CH.sub.3                                                                          H  H CH.sub.3                                                                           H OC.sub.2 H.sub.5                                 CH.sub.3                                                                            CH.sub.3                                                                             CH.sub.3                                                                          H  H NO.sub.2                                                                           H OC.sub.2 H.sub.5                                 CH.sub.3                                                                            CH.sub.3                                                                             H   H  H H    H CF.sub.3                                         C.sub.2 H.sub.5                                                                     CH.sub.3                                                                             F   H  H H    H OCH.sub.2 CH.sub.2 OCH.sub.3                     C.sub.2 H.sub.5                                                                     CH.sub.3                                                                             Br  H  H H    H n-C.sub.3 H.sub.7 O                              C.sub.2 H.sub.5                                                                     CH.sub.3                                                                             OCH.sub.3                                                                         H  H OCH.sub.3                                                                          H Cl                                               CH.sub.3                                                                            C.sub.2 H.sub.5                                                                      Cl  H  F H    H OC.sub.2 H.sub.5                                 C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                                                                      NO.sub.2                                                                          H  H CH.sub.3                                                                           H CH.sub.2 OCH.sub.3                               n-C.sub.3 H.sub.7                                                                   CH.sub.3                                                                             Cl  H  H H    Cl                                                                              SCH.sub.3                                        n-C.sub.3 H.sub.7                                                                   CH.sub.3                                                                             OCH.sub.3                                                                         H  H Cl   H OC.sub.2 H.sub.5                                 CH(CH.sub.3).sub.2                                                                  CH.sub.3                                                                             F   H  H H    F OCH(CH.sub. 3).sub.2                             CH(CH.sub.3).sub.2                                                                  CH.sub.3                                                                             Cl  H  H NO.sub.2                                                                           H OC.sub.2 H.sub.5                                 OCH.sub.3                                                                           CH.sub.3                                                                             Br  H  H H    H OC.sub.2 H.sub.5                                 CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                    Cl  H  H Cl   H OC.sub.2 H.sub.5                                 H     n-C.sub.3 H.sub.7                                                                    NO.sub.2                                                                          H  H H    H OC.sub.2 H.sub.5                                 H     CH(CH.sub.3).sub.2                                                                   CF.sub.3                                                                          H  H H    H OC.sub.2 H.sub.5                                 CH.sub.3                                                                            CH(CH.sub.3).sub.2                                                                   Cl  H  H H    H OC.sub.2 H.sub.5                                 __________________________________________________________________________

By using an appropriateN-(1,3,5-triazin-2-yl)-N-aminocarbonyl-2-thiophenesulfonamide orN-(pyrimidin-2-yl)-N-aminocarbonyl-2-thiophenesulfonamide, the compoundsof Formula I set forth in Table V can be prepared by the procedure ofExample 6. Alternatively, by using an appropriately substitutedsulfonyl-N-alkyl-2-thiophenecarbamyl chloride and an appropriatelysubstituted-2-aminopyrimidine or 2-amino-1,3,5-triazine, the samecompounds of Formula I can be prepared by the procedure of Example 7.

                  TABLE V                                                         ______________________________________                                         ##STR38##                                                                      R.sub.1    R.sub.2    X          Y      Z                                   ______________________________________                                        H        CH.sub.3   CH.sub.3     CH.sub.3                                                                             CH                                    H        CH.sub.3   OCH.sub.3    CH.sub.3                                                                             CH                                    H        CH.sub.3   OCH.sub.3    OCH.sub.3                                                                            CH                                    CH.sub.3 CH.sub.3   CH.sub.3     CH.sub.3                                                                             CH                                    CH.sub.3 CH.sub.3   OCH.sub.3    CH.sub.3                                                                             CH                                    CH.sub.3 CH.sub.3   OCH.sub.3    OCH.sub.3                                                                            CH                                    C.sub.2 H.sub.5                                                                        CH.sub.3   CH.sub.3     CH.sub.3                                                                             CH                                    C.sub.2 H.sub.5                                                                        CH.sub.3   OCH.sub.3    CH.sub.3                                                                             CH                                    n-C.sub.3 H.sub.7                                                                      CH.sub.3   OCH.sub.3    OCH.sub.3                                                                            CH                                    CH(CH.sub.3).sub.2                                                                     CH.sub.3   OCH.sub.3    CH.sub.3                                                                             CH                                    OCH.sub.3                                                                              CH.sub.3   OCH.sub.3    CH.sub.3                                                                             CH                                    CH.sub.3 C.sub.2 H.sub.5                                                                          OCH.sub.3    CH.sub.3                                                                             CH                                    CH.sub.3 C.sub. 2 H.sub.5                                                                         OCH.sub.3    OCH.sub.3                                                                            CH                                    C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                          OCH.sub.3    CH.sub.3                                                                             CH                                    H        CH.sub.3   CH.sub.3     CH.sub.3                                                                             N                                     H        CH.sub.3   OCH.sub.3    CH.sub.3                                                                             N                                     H        CH.sub.3   OCH.sub.3    OCH.sub.3                                                                            N                                     CH.sub.3 CH.sub.3   CH.sub.3     CH.sub.3                                                                             N                                     CH.sub.3 CH.sub.3   OCH.sub.3    OCH.sub.3                                                                            N                                     CH.sub.3 CH.sub.3   OCH.sub.3    CH.sub.3                                                                             N                                     C.sub.2 H.sub.5                                                                        CH.sub.3   OCH.sub.3    OCH.sub.3                                                                            N                                     C.sub.2 H.sub.5                                                                        CH.sub.3   OCH.sub.3    CH.sub.3                                                                             N                                     n-C.sub.3 H.sub.7                                                                      CH.sub.3   OCH.sub.3    OCH.sub.3                                                                            N                                     CH(CH.sub.3).sub.2                                                                     CH.sub.3   OCH.sub.3    OCH.sub.3                                                                            N                                     OCH.sub.3                                                                              CH.sub.3   OCH.sub.3    CH.sub.3                                                                             N                                     CH.sub.3 C.sub.2 H.sub.5                                                                          CH.sub.3     CH.sub.3                                                                             N                                     C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                          OCH.sub.3    OCH.sub.3                                                                            N                                     H        C.sub.2 H.sub.5                                                                          OCH.sub.3    CH.sub.3                                                                             CH                                    H        C.sub.2 H.sub.5                                                                          OCH.sub.3    OCH.sub.3                                                                            N                                     H        CH.sub.3   CH.sub.2 OCH.sub.3                                                                         OCH.sub.3                                                                            CH                                    H        CH.sub.3   CF.sub.3     CH.sub.3                                                                             CH                                    H        C.sub.2 H.sub.5                                                                          SCH.sub.3    CH.sub.3                                                                             CH                                    CH.sub.3 C.sub. 2 H.sub.5                                                                         OC.sub.2 H.sub.5                                                                           OCH.sub.3                                                                            CH                                    H        CH.sub.3   OC.sub.2 H.sub.5                                                                           OCH.sub.3                                                                            N                                     H        CH.sub.3   SCH.sub.3    OCH.sub.3                                                                            N                                     H        C.sub.2 H.sub.5                                                                          OCH.sub.2 CH.sub.2 OCH.sub.3                                                               OCH.sub.3                                                                            N                                     CH.sub.3 CH.sub.3   n-C.sub.3 H.sub.7 O                                                                        CH.sub.3                                                                             CH                                    C.sub.2 H.sub.5                                                                        CH.sub.3   Cl           OCH.sub.3                                                                            N                                     CH.sub.3 n-C.sub.3 H.sub.7                                                                        OCH.sub.3    CH.sub.3                                                                             CH                                    H        n-C.sub.3 H.sub.7                                                                        OCH.sub.3    OCH.sub.3                                                                            N                                     H        CH(CH.sub.3).sub.2                                                                       OCH.sub.3    CH.sub.3                                                                             CH                                    CH.sub.3 CH(CH.sub.3).sub.2                                                                       OCH.sub.3    OCH.sub.3                                                                            N                                     ______________________________________                                    

Useful formulations of the compounds of Formala I can be prepared inconventional ways. They include dusts, granules, pellets, solutions,suspensions, emulsions, wettable powders, emulsifiable concentrates andthe like. Many of these may be applied directly. Sprayable formulationscan be extended in suitable media and used at spray volumes of form afew pints to several hundred gallons per acre. High strengthcompositions are primarily used as intermediates for furtherformulation. The formulations, broadly, contain about 1% to 99% byweight of active ingredient(s) and at least one of (a) about 0.1% to 20%surfactant(s) and (b) about 1% to 99% solid or liquid diluent(s). Morespecifically, they will contain these ingredients in the followingapproximate proportions:

                  TABLE VI                                                        ______________________________________                                                    PERCENT BY WEIGHT                                                             Active                                                                        Ingredient                                                                            Diluent(s)                                                                              Surfactant(s)                                   ______________________________________                                        Wettable powders                                                                            20-90      0-74     1-10                                        Oil Suspensions,                                                                             5-50     40-95     0-15                                        Emulsions, Solutions                                                          (including Emulsifiable                                                       concentrates)                                                                 Aqueous Suspensions                                                                         10-50     40-84     1-20                                        Dusts          1-25     70-99     0-5                                         Granules and Pellets                                                                         1-95      5-99     0-15                                        High Strength 90-99      0-10     0-2                                         Compositions                                                                  ______________________________________                                    

Lower or higher levers of active ingredient can, of course, by presentdepending on the intended use and the physical properties of thecompound. Higher ratios of surfactant to active ingredient are sometimesdesirable, and are achieved by incorporation into the formulation or bytank mixing.

Typical solid diluents are described in Watkins, et al, "Handbook ofInsecticide Dust Diluents and Carriers", 2nd, Ed., Dorland Books,Caldwell, N.J. The more absorptive diluents are preferred for wettablepowders and the denser ones for dusts. Typical liquid diluents andsolvents are described in Marsden, "Solvents Guide", 2nd. Ed.,Interscience, New York, 1950 Solubility under 0.1% is preferred forsuspension concentrates; solution concentrates are preferably stableagainst phase separation at 0° C. "McCutcheon's Detergents andEmulsifiers Annual", MC Publishing Co., Ridgewood, N.J., as well asSisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publ.Co., New York, 1964, list surfactants and recommended uses. Allformulations can contain minor amounts of additives to reduce foam,caking, corrosion, microbiological growth, etc. Preferably, ingredientsshould be approved by the U.S. Environmental Protection Agency for theuse intended.

The methods of making such compositions are well known. Solutions areprepared by simply mixing the ingredients. Fine solid compositions aremade by blending and, usually, grinding as in a hammer or fluid energymill. Suspensions are prepared by wet milling (see, for example,Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made byspraying the active material upon preformed granular carriers or byagglomeration techniques. See J. E. Browning, "Agglomeration", ChemicalEngineering, Dec. 4, 1967, pp. 147ff. and "Perry's Chemical Engineer'sHandbook", 4th Ed., McGraw-Hill, N.Y. 1963, pp 8-59ff.

For further information regarding the art of formulation, see forexample:

H. M. Loux, U.S. Pat. No. 3,235,361, Feb. 15, 1966, Col. 6, Line 16through Col. 7, Line 19 Examples 10-41.

R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Mar. 14, 1967, Col. 5, Line43 through Col. 7 Line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58,132, 138-140, 162-164, 166, 167, 169-182.

H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, June 23, 1959, Col. 3Line 66 through Col. 5 Line 17 and Examples 1-4.

G. C. Klingman, "Weed Control as a Science", John Wiley & Sons, Inc.,New York, 1961 pp. 81-96.

J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed. BlackwellScientific Publications, Oxford, 1968, pp. 101-103.

EXAMPLE 8

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        N--[N--(4,6-dimethoxy-1,3,5-triazin-                                                                 25%                                                    2-yl)-N--methylaminocarbonyl]-2-                                              chlorobenzenesulfonamide                                                      Dioctyl sodium sulfosuccinate                                                                        1.5%                                                   Sodium ligninsulfonate  3%                                                    Low viscosity methyl cellulose                                                                       1.5%                                                   Attapulgite            69%                                                    ______________________________________                                    

The ingredients are thoroughly blended, passed through an air mill, toproduce an average particle size under 15 microns, reblended, and siftedthrough a U.S.S. No. 50 sieve (0.3 mm opening) before packaging.

EXAMPLE 9

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        N--[N--(4-methoxy-6-methylpyrimidin-                                                                  50%                                                   2-yl)-N--methylaminocarbonyl]-2-                                              chlorobenzenesulfonamide                                                      Sodium alkylnaphthalenesulfonate                                                                       2%                                                   Low viscosity methyl cellulose                                                                         2%                                                   Diatomaceous earth      46%                                                   ______________________________________                                    

The ingredients are blended, coarsely hammer-milled and then air milledto produce particles of active essentially all below 10 microns indiameter. The product is reblended before packaging.

EXAMPLE 10

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        N--[N--(4,6-dimethoxy-1,3,5-triazin-                                                                 80%                                                    2-yl)-N--methylaminocarbonyl]-2-                                              nitrobenzenesulfonamide                                                       Sodium alkylnaphthalenesulfonate                                                                     2%                                                     Sodium ligninsulfonate 2%                                                     Synthetic amorphous silica                                                                           3%                                                     Kaolinite              13%                                                    ______________________________________                                    

The ingredients are blended and hammer-milled to produce particlesessentially all below 100 microns. The product is reblended, siftedthrough a U.S.S. No. 50 mesh screen and packaged.

EXAMPLE 11

    ______________________________________                                        High Strength Concentrate                                                     ______________________________________                                        N--[N--(4-methoxy-6-methylpyrimidin-                                                                  98.5%                                                 2-yl)-N--methylaminocarbonyl]-2-                                              nitrobenzenesulfonamide                                                       Silica aerogel          0.5%                                                  Synthetic amorphous fine silica                                                                       1.0%                                                  ______________________________________                                    

The ingredients are blended and ground in a hammer mill to produce ahigh strength concentrate essentially all passing a U.S.S. No. 50 sieve(0.3 mm opening). This material may then be formulated in a variety ofways.

EXAMPLE 12

    ______________________________________                                        Aqueous Suspensions                                                           ______________________________________                                        N--[N--(4-methoxy-6-methylpyrimidin-                                                                  40%                                                   2-yl)-N--methylaminocarbonyl]-2-                                              nitrobenzenesulfonamide                                                       Polyacrylic acid thickener                                                                            0.3%                                                  Dodecylphenol polyethylene glycol ether                                                               0.5%                                                  Disodium phosphate      1.0%                                                  Monosodium phosphate    0.5%                                                  Polyvinyl alcohol       1.0%                                                  Water                   56.7%                                                 ______________________________________                                    

The ingredients are ground together in a sand mill to produce particlesessentially all under five microns in size.

EXAMPLE 13

    ______________________________________                                        Oil Suspension                                                                ______________________________________                                        N--[N--(4,6-dimethoxy-1,3,5-triazin-2-                                                               25%                                                    yl)-N--methylaminocarbonyl]-2-                                                nitrobenzenesulfonamide                                                       Polyoxyethylene sorbitol hexaoleate                                                                   5%                                                    Highly aliphatic hydrocarbon oil                                                                     70%                                                    ______________________________________                                    

The ingredients are ground together in a sand mill until the solidparticles have been reduced to under about 5 microns. The resultingsuspension may be applied directly, but preferably after being extendedwith oils or emulsified in water.

EXAMPLE 14

    ______________________________________                                        Oil Suspension                                                                ______________________________________                                        N--[N--(4-methoxy-6-methylpyrimidin-2-yl-                                                              35%                                                  N--methylaminocarbonyl]-2-chlorobenzene-                                      sulfonamide                                                                   Blend of polyalcohol carboxylic esters                                                                  6%                                                  and oil soluble petroleum sulfonates                                          Xylene                   59%                                                  ______________________________________                                    

The ingredients are combined and ground together in a sand mill toproduce particles essentially all below 3 microns. The product can beused directly, extended with oils, or emulsified in water.

EXAMPLE 15

    ______________________________________                                        Granule                                                                       ______________________________________                                        N--[N--(4,6-dimethoxy-1,3,5-triazin-2-yl)-                                                              1%                                                  N--methylaminocarbonyl]-2-                                                    chlorobenzenesulfonamide                                                      Attapulgite granules (low volative matter,                                                             99%                                                  0.71/0.31 mm U.S.S. # 25-50 sieves)                                           ______________________________________                                    

The active ingredient is warmed to approximately 80° C. and sprayed upondedusted and pre-warmed attapulgite granules in a double-cone blender.The granules are then allowed to cool and are packaged.

EXAMPLE 16

    ______________________________________                                        Granule                                                                       ______________________________________                                        Wettable powder of Example 9                                                                          5%                                                    Attapulgite granules (U.S.S. # 20-40;                                                                95%                                                    0.84-0.42 mm)                                                                 ______________________________________                                    

A slurry of wettable powder containing 50% solids is sprayed on thesurface of attapulgite granules in a double-cone blender. The granulesare dried and packaged.

EXAMPLE 17

    ______________________________________                                        Extruded Pellet                                                               ______________________________________                                        N--[N--(4,6-dimethoxy-1,3,5-triazin-2-yl)-                                                             25%                                                  N--methylaminocarbonyl]-2-nitrobenzene-                                       sulfonamide                                                                   Anhydrous soidum sulfate 10%                                                  Crude calcium ligninsulfonate                                                                           5%                                                  Sodium alkylnaphthalenesulfonate                                                                        1%                                                  Calcium/magnesium bentonite                                                                            59%                                                  ______________________________________                                    

The ingredients are blended, hammer milled and then moistened with about12% water. The mixture is extruded as cylinders about 3 mm diameterwhich are cut to produce pellets about 3 mm long. These may be useddirectly after drying, or the dried pellets may be crushed to pass aU.S.S. No. 20 sieve (0.84 mm opendings). The granules held on a U.S.S.No. 40 sieve (0.42 mm openings) may be packaged for use and the finesrecycled.

UTILITY

The compounds of Formula I are useful for the selective control ofundesired vegetation in crops such as rice, wheat, and barley. Thesecompounds are most effective when applied after emergence of weeds fromthe soil. However, they are also effective when applied preemergence. Inaddition, they can be used as directed treatments for thepre/post-emergence control of weeds in various crops. These compoundsare also useful wherever general weed control is required, such asindustrial sites, railroad and utility rights-of-way, along fences,building foundations, parking and storage lots, etc.

The precise amount of the compounds of Formula I to be used in any givensituation will vary according to the particular end result desired, theuse involved, the crop weed species, and soil involved, the formulationused, the mode of application, prevailing weather conditions, foliagedensity and the like factors. Since so many variables play a role, it isnot possible to state a rate of application suitable for all situations.Broadly speaking, the compounds of the invention are used at levels ofabout 0.03 to about 15 kilograms, preferably about 0.12 to about 8, perhectare. The lower rates in this range will generally be selected onlighter soils, soils low in organic matter content, for selective weedcontrol in crops, or in situations where maximum persistance is notnecessary.

Although the compounds of the present invention provide excellent weedcontrol when applied in the sole herbicide treatment, they may beadvantageously applied in combination with other herbicides, including,but not restricted to, the following:

Methyl-2-//4-/2,4-dichlorophenoxy/phenoxy//-propanoate;

Carbamic acid diisopropylthiol-S-/2,3,3-trichloroalkyl/ester;

1,2-dimethyl-3,5-diphenyl-pyrazolium methyl-sulfate;

Ethyl-N-benzoyl-N-/3,4-dichlorophenyl-2-aminopropanoate;

Diisopropylthiolcarbamic acid, ester with 2,3-dichloroallyl alcohol;

4-Chloro-2-butynyl-m-chlorocarbanilate;

2,4-dichlorophenoxyacetic acid (and derivatives);

3-chloro-2-(4-chloro-2-fluorophenyl)-4,5,6,7-tetrahydro-2H-indazole;

3-isopropyl-1(H)-benzo-2,1,3-thiadizin-4-one-2,2-dioxide;

S-(4-chlorobenzyl)-N,N-diethylthiolcarbamate;

2-chloro-2',6'-diethyl-N-butoxymethyl-acetanilide;

3',4'-dichloropropionanilide;

2,4,6-trichlorophenyl-4'-nitrophenyl ether;

5-tert-butyl-3-(2,4-dichloro-5-isopropoxyphenyl)-1,3,4-oxadiazol-2-one

The herbicidal activity of compounds of this invention was discovered ingreenhouse tests, conducted as explained below.

Test 1

Seeds of crabgrass (Digitaria spp.), barnyardgrass (Echinochloacrusgalli), wild oats (Avena fatua), Cassia Tora, morningglory (Ipomoeaspp.), cocklebur (Xanthium spp.), sorghum, corn, soybean, rice, wheatand nutsedge tubers were planted in a growth medium and treatedpreemergence with the chemicals dissolved in a non-phytotoxic solvent.At the same time, cotton having five leaves (including cotyledonaryones), bush beans with the third trifoliolate leaf expanding, crabgrasswith two leaves, barnyardgrass with two leaves, wild oats with one leaf,cassia with three leaves (including cotyledonary ones), morningglorywith four leaves (including the cotyledonary ones), cocklebur with fourleaves (including the cotyledonary ones), sorghum with three leaves,corn with three leaves, soybean with two cotyledonary leaves, rice withtwo leaves, wheat with one leaf, and nutsedge with three-five leaveswere sprayed. Treated plants and controls were maintained in agreenhouse for sixteen days, then all species were compared to controlsand visually rated for response to treatment.

The ratings for compounds tested by this procedure are recorded in TableVII, and consists of a number and a letter. The number describes theextent of the response and ranges from zero to ten, with zerorepresenting no response and ten representing 100% response. The letterdescribes the type of response, with "B" representing burn (acuteresponse), "C" chlorosis-necrosis (chronic response), "E" emergenceinhibited, "G" growth retarded, "H" formative effect (malformation orhormone type), "L" lodging, and "U" unusual pigmentation (other thandark green color). However, the combined rating "6Y" is an exception tothe extent and type explanation given above, in that it simplyrepresents abscised buds or flowers.

      POST EMERGENCE      ##STR39##      Rate, kg/ha BEANBUSH COTTON GHUMSOR- CORN BEANSOY- WHEAT OATSWILD RICE     GRASSYARDBARN- GRASSCRAB- GLORYING-MORN- COCKLEBUR CASSIA SEDGENUT-      ##STR40##      2 4H 2U 2C9G 0 7H 6C9G 0 0 0 1C9H 4G 5C9G 9C 5C9G 4C9G  NO.sub.2 2 3C     9C 4G 3C 3C 1C 2C 1C 5C 4C 9C 9C 9C 5C   8G   9G 9G   6G 9G 8G    8G     6Y  .4 4H 9C 2G 3H 4C 0 0 3G 2C 9C 9C 9C 8C 5C   6G   9G 9G    7G     8G       6Y      ##STR41##      2 1C 1C1H 0 0 0 0 0 0 0 0 0 0 0 0      PRE-EMERGENCE     ##STR42##      Rate, kg/ha SORGHUM CORN SOYBEAN WHEAT OATSWILD RICE GRASSYARDBARN-     GRASSCRAB- GLORYMORNING- COCKLEBUR CASSIA SEDGENUT-      ##STR43##      2 0 3G 9H 0 0 1C3G 3C9H 4G &E 9H &E 5G  NO.sub.2 2 5G 2C 9H 0 2C &E 2C     9G 9G 9E 9G &E    7G     9G  .4 0 1C 9H 0 2G 9H 2C 1C 9G 9G 9G &E    9G        9G 5G      ##STR44##      2 0 2C 1C 0 0 2G 2G 0 1C 0 2C 0

Test 2

The data from Test 2 are presented in Table VIII to illustrate furtherthe biological activity of the compounds of this invention. Theyillustrate the herbicidal efficacy of the compounds with selectivity foran important crop rice.

The test compounds were applied in a non-phytotoxic solvent to soil potscontaining seeds of an intermediate hybrid rice, japonica rice,barnyardgrass (Echinochloa crusgalli), and morningglory (Ipomoea sp.).Established plantings (postemergence) of the species mentioned abovewere also included in the test. The plants were maintained in agreenhouse (glasshouse), and visual plant response ratings (as describedfor Table VII) were taken four weeks after application.

                                      TABLE VIII                                  __________________________________________________________________________                               Preemergence      Postemergence                                               Inter-    Barn-                                                                             Morn-                                                                             Inter-    Barn-                                                                             Morn-                                         mediate                                                                            Japonica                                                                           yard-                                                                             ing-                                                                              mediate                                                                            Japonica                                                                           yard-                                                                             ing-               COMPOUND             kg ai/ha                                                                            Rice Rice grass                                                                             glory                                                                             Rice Rice grass                                                                             glory              __________________________________________________________________________     ##STR45##           1/4 1/2 1 2                                                                         0 0 0 0                                                                            0 0 0 0                                                                            0 0 0 0                                                                           0 0 0 0                                                                           0 0 0 0                                                                            0 0 0 0                                                                            0 0 0 4G                                                                          10B 10B 10B                                                                   10B                 ##STR46##           1/8 1/4 1/2 1                                                                       0 0 0 0                                                                            0 0 0 0                                                                            0 0 0 0                                                                           0 0 0 0                                                                           0 0 0 0                                                                            0 0 0 0                                                                            0 0 0 6B5L                                                                        10B 10B 10B        __________________________________________________________________________                                                               10B            

What is claimed is:
 1. A compound having the formula: ##STR47## whereinR₁ is H, alkyl of one to three carbon atoms or --OCH₃ ;R₂ is H or alkylof one to three carbon atoms; R₃ is ##STR48## X is Cl, CH₃, --CH₂ CH₃,alkoxy of one to three carbons, CF₃, CH₃ S--, CH₃ OCH₂ -- or CH₃ OCH₂CH₂ O--; Y is CH₃ or OCH₃ ; and Z is N;and their agriculturally suitablesalts; provided that: a. R₁ and R₂ may not simultaneously be hydrogen.2. A compound of claim 1 whereinR₁ and R₂ are independently H or CH₃ ; Xis CH₃, CH₃ CH₂ -- or alkoxy of one to three carbons; and Y is CH₃ orOCH₃.
 3. A compound of claim 2 whereinR₁ is CH₃ ; R₂ is H; and X and Yare independently CH₃ or OCH₃.
 4. A compound of claim 3 whereinX is OCH₃; and Y is CH₃ or OCH₃.
 5. A composition suitable for controlling thegrowth of undesired vegetation which comprises an effective amount of acompound of chain 1 and at least one of the following: surfactant, solidor liquid diluent.
 6. A composition suitable for controlling the growthof undesired vegetation which comprises an effective amount of acompound of claim 1 and at least one of the following: surfactant, solidor liquid diluent.
 7. A composition suitable for controlling the growthof undesired vegetation which comprises an effective amount of acompound of claim 3 and at least one of the following: surfactant, solidor liquid diluent.
 8. A composition suitable for controlling the growthof undesired vegetation which comprises an effective amount of acompound of claim 4 and at least one of the following: surfactant, solidor liquid diluent.
 9. A method for controlling the growth of undesiredvegetation which comprises applying to the locus to be protected aneffective amount of a compound of claim
 1. 10. A method for controllingthe growth of undesired vegetation which comprises applying to the locusto be protected an effective amount of a compound of claim
 2. 11. Amethod for controlling the growth of undesired vegetation whichcomprises applying to the locus to be protected an effective amount of acompound of claim
 3. 12. A method for controlling the growth ofundesired vegetation which comprises applying to the locus to beprotected an effective amount of a compound of claim 4.